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1

Valine entry into rat brain after diet-induced changes in plasma amino acids  

SciTech Connect

Passage of amino acids across the blood-brain barrier is assumed to be modified by amino acid composition of the blood. To gain a better understanding of the effects of protein intake on brain amino acid uptake, the authors examined associations among diet, plasma amino acid patterns, and the rate of entry of valine into the brain. Rats were fed diets containing 6, 18, or 50% casein before receiving one meal of a diet containing 0, 6, 18, or 50% casein. After 4-7 h, they were anesthetized and infused intravenously with (/sup 14/C)valine for 5 min before plasma and brain samples were taken for determination of radioactivity and content of individual amino acids. As protein content of the meal was increased from 0 to 50% casein, plasma and brain concentrations of valine and most other large neutral amino acid (LNAA) increased severalfold; also the ratio of (/sup 14/C)valine in brain to that in plasma decreased by >50%, and the rate of valine entry into the brain increased 3.5-fold. The increase in valine flux slowed as plasma levels of LNAA, competitors for valine transport, increased. The results were far more dependent on protein content of the final meal than on that of the adaptation diet; thus changes in protein intake, as reflected in altered plasma amino acid patterns, markedly altered valine entry into the brain.

Tews, J.K.; Greenwood, J.; Pratt, O.E.; Harper, A.E.

1987-01-01

2

Anthropometry and plasma valine, amino acids, and proteins in the nutritional assessment of hemodialysis patients  

Microsoft Academic Search

Anthropometry and plasma valine, amino acids, and proteins in the nutritional assessment of hemodialysis patients. Non-fasting plasma amino acids, proteins, anthropometric measurements, urea, and creatinine for 17 hemodialysis patients were compared with values in normal patients of similar age and sex. Values were characteristic for renal failure but with similarities to protein-energy malnutrition. Partial correlation coefficients, correcting for age and

Gerald A Young; Charles R Swanepoel; Martyn R Croft; Shirley M Hobson; Frank M Parsons

1982-01-01

3

The Effects of Test Doses of Leucine, Isoleucine or Valine on Plasma Amino Acid Levels The Unique Effect of Leucine  

Microsoft Academic Search

AND ERNST J. DRENICK, M.D.? T HE OBSERVATION that proportions of the branched chain amino acids were increased in the plasma of severely obese subjects during the postabsorption period' prompted an in- vestigation to determine the effects of the oral administration of test doses of leucine, isoleucine or valine on plasma amino acid levels in obese and normal weight subjects.

MARIAN E. SWENDSEID; JUANITA VILLALOBOS; WILLIAM S. FIGUEROA

4

Influence of valine and other amino acids on total diacetyl and 2,3-pentanedione levels during fermentation of brewer's wort.  

PubMed

Undesirable butter-tasting vicinal diketones are produced as by-products of valine and isoleucine biosynthesis during wort fermentation. One promising method of decreasing diacetyl production is through control of wort valine content since valine is involved in feedback inhibition of enzymes controlling the formation of diacetyl precursors. Here, the influence of valine supplementation, wort amino acid profile and free amino nitrogen content on diacetyl formation during wort fermentation with the lager yeast Saccharomyces pastorianus was investigated. Valine supplementation (100 to 300 mg L(-1)) resulted in decreased maximum diacetyl concentrations (up to 37 % lower) and diacetyl concentrations at the end of fermentation (up to 33 % lower) in all trials. Composition of the amino acid spectrum of the wort also had an impact on diacetyl and 2,3-pentanedione production during fermentation. No direct correlation between the wort amino acid concentrations and diacetyl production was found, but rather a negative correlation between the uptake rate of valine (and also other branched-chain amino acids) and diacetyl production. Fermentation performance and yeast growth were unaffected by supplementations. Amino acid addition had a minor effect on higher alcohol and ester composition, suggesting that high levels of supplementation could affect the flavour profile of the beer. Modifying amino acid profile of wort, especially with respect to valine and the other branched-chain amino acids, may be an effective way of decreasing the amount of diacetyl formed during fermentation. PMID:23677441

Krogerus, Kristoffer; Gibson, Brian R

2013-08-01

5

Synthesis and characterization of novel, optically active polyamides derived from S -valine natural amino acid and bulky anthracenic side chain  

Microsoft Academic Search

This is the first description of the application of molten tetrabutylammonium bromide (TBAB) in the presence of triphenyl\\u000a phosphite (TPP) for the synthesis of novel polyamides (PAs). Monomer diacid, 5-[(9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximido)-3-methylbutanoylamino]isophthalic\\u000a acid (4), having anthracenic and amino acid S-valine pendant group, was synthesized in four steps. Several novel, optically active\\u000a PAs were prepared by the condensation of synthesized diacid monomer 4

Fatemeh Mirkarimi

2010-01-01

6

Thermal, Dielectric Studies on Pure and Amino Acid L-Glutamic Acid, L-Histidine L-Valine Doped Potassium Dihydrogen Phosphate Single Crystals  

NASA Astrophysics Data System (ADS)

Amino acids (L-Glutamic acid, L-Histidine, L-Valine) doped potassium dihydrogen phosphate crystals were grown by the solution growth technique. Slow cooling as well as slow evaporation methods were employed to grow these crystals. The concentration of dopants in the mother solution was varied from 0.1 mole % to 10 mole %. The solubility data for all dopant concentrations were determined. The variation in pH and the corresponding habit modification of the grown crystals were characterized with UV - VIS, FT-IR and SHG trace elements, and dielectric studies reveal slight distortion of lattice parameter for the heavily doped KDP crystals. TGA-DTA studies reveal good thermal stability. The dopants increase the hardness value of the material, which also depends on the concentration of the dopants. Amino acids doping improved the NLO properties. The detailed results on the spectral parameters, habit modifications and constant values will be presented.

Kumaresan, P.; Babu, S. Moorthy; Anbarasan, P. M.

7

Growth of Transplastomic Cells Expressing d-Amino Acid Oxidase in Chloroplasts Is Tolerant to d-Alanine and Inhibited by d-Valine1[W][OA  

PubMed Central

Dual-conditional positive/negative selection markers are versatile genetic tools for manipulating genomes. Plastid genomes are relatively small and conserved DNA molecules that can be manipulated precisely by homologous recombination. High-yield expression of recombinant products and maternal inheritance of plastid-encoded traits make plastids attractive sites for modification. Here, we describe the cloning and expression of a dao gene encoding d-amino acid oxidase from Schizosaccharomyces pombe in tobacco (Nicotiana tabacum) plastids. The results provide genetic evidence for the uptake of d-amino acids into plastids, which contain a target that is inhibited by d-alanine. Importantly, this nonantibiotic-based selection system allows the use of cheap and widely available d-amino acids, which are relatively nontoxic to animals and microbes, to either select against (d-valine) or for (d-alanine) cells containing transgenic plastids. Positive/negative selection with d-amino acids was effective in vitro and against transplastomic seedlings grown in soil. The dual functionality of dao is highly suited to the polyploid plastid compartment, where it can be used to provide tolerance against potential d-alanine-based herbicides, control the timing of recombination events such as marker excision, influence the segregation of transgenic plastid genomes, identify loci affecting dao function in mutant screens, and develop d-valine-based methods to manage the spread of transgenic plastids tagged with dao.

Gisby, Martin F.; Mudd, Elisabeth A.; Day, Anil

2012-01-01

8

Conversion of ammonia or urea into essential amino acids, L -leucine, L -valine, and L -isoleucine using artificial cells containing an immobilized multienzyme system and dextran-NAD +  

Microsoft Academic Search

A multienzyme system consisting of leucine dehydrogenase (EC 1.4.1.9), L-lactic dehydrogenase (EC 1.1.1.27), urease (EC 3.5.1.5),\\u000a and dextran-NAD+ was microencapsulated within artificial cells. This system could convert ammonia and urea into essential amino acids,L-leucine,L-valine, andL-isoleucine.L-lactate acted as a cosubstrate for the regeneration of dextran-NADH. Greater concentrations of L-lactate favored the higher\\u000a conversion ratios. The effects of ammonium salts and urea

Kang Fu Gu; Thomas Ming Swi Chang

1990-01-01

9

Thermal, dielectric studies on pure and amino acid ( L-glutamic acid, L-histidine, L-valine) doped KDP single crystals  

NASA Astrophysics Data System (ADS)

Amino acids ( L-glutamic acid, L-histidine, L-valine) doped potassium dihydrogen phospate crystals are grown by solution growth technique. Slow cooling as well as slow evaporation methods were employed to grow these crystals. The concentration of dopants in the mother solution was varied from 0.1 mol% to 10 mol%. The solubility data for all dopants concentration were determined. There is variation in pH value and hence, there is habit modification of the grown crystals were characterized with UV-VIS, FT-IR studies, SHG trace elements and dielectric studies reveal slight distortion of lattice parameter for the heavily doped KDP crystals. UV-Visible spectra confirm the improvement in the transparency of these crystals on doping metal ions. FT-IR spectra reveal strong absorption band between 1400 and 1600 cm -1 for metal ion doped crystals. TGA-DTA studies reveal good thermal stability. The dopants increase the hardness value of the material and it also depends on the concentration of the dopants. Amino acids doping improved the NLO properties. The detailed results on the spectral parameters, habit modifications and constant values will be presented.

Kumaresan, P.; Moorthy Babu, S.; Anbarasan, P. M.

2008-05-01

10

Enhanced intracellular accumulation of a non-nucleoside anti-cancer agent via increased uptake of its valine ester prodrug through amino acid transporters.  

PubMed

The phenomenon known as multiple-drug resistance, whereby anti-cancer agents are expelled from cancer cells, makes it necessary to develop methods that will reliably increase the accumulation of anti-cancer agents within cancer cells. To accomplish this goal, a new model compound, Val-SN-38, was synthesized by introducing valine to SN-38, an active ingredient of irinotecan. Val-SN-38 improved intracellular accumulation approximately 5-fold in MCF7 cells, compared with SN-38, and rather than changes in membrane permeability, the amino acid transporter ATB(0,+) played a role, whereas the dipeptide transporter PEPT1 did not. Other sodium-dependent amino acid transporters, namely ATA1, ATA2, and ASCT2, were unexpectedly involved in the uptake of Val-SN-38 as well. The efflux of Val-SN-38 by major efflux transporters was variably changed, but not significantly. In summary, the enhanced accumulation of Val-SN-38 in cancer cells was due to augmented uptake via various amino acid transporters. The results of the present study make a compelling argument in favour of a prodrug concept that can improve intracellular accumulation and take advantage of amino acid transporters without significantly inducing multiple-drug resistance. PMID:22233275

Kwak, Eun-Young; Shim, Won-Sik; Chang, Ji-Eun; Chong, Saeho; Kim, Dae-Duk; Chung, Suk-Jae; Shim, Chang-Koo

2012-07-01

11

Synthesis and characterization of novel, optically active polyamides derived from S-valine natural amino acid and bulky anthracenic side chain.  

PubMed

This is the first description of the application of molten tetrabutylammonium bromide (TBAB) in the presence of triphenyl phosphite (TPP) for the synthesis of novel polyamides (PAs). Monomer diacid, 5-[(9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximido)-3-methylbutanoylamino]isophthalic acid (4), having anthracenic and amino acid S-valine pendant group, was synthesized in four steps. Several novel, optically active PAs were prepared by the condensation of synthesized diacid monomer 4 with various aromatic diamines using two different techniques: a mixture of N-methyl-2-pyrrolidone (NMP)/TPP/pyridine/calcium chloride (method I) and combination of TPP with TBAB (method II). The main goal of the present paper was to prepare novel PAs in a green media by removal of toxic reagents. Therefore, TBAB/TPP was used as a novel, easy, safe and eco-friendly method for the preparation of aromatic PAs. This method is compared with the polymerization reaction under conventional solvent and in the case of TBAB as a new method, higher yields, inherent viscosities and thermally stable of PAs are gained. The resulting polymers showed good solubility in polar aprotic solvents such as dimethyl sulfoxide, NMP, N,N-dimethylacetamide and N,N-dimethylformamide. These polymers are characterized with respect to chemical structure and purity by means of specific rotation experiments, FT-IR, 1H NMR spectroscopy techniques and elemental analysis. The obtained PAs exhibit good thermal stability up to 335°C for 10% weight loss in nitrogen atmosphere and glass transition temperatures fell in the rang of 177-185°C. PMID:20352462

Mallakpour, Shadpour; Mirkarimi, Fatemeh

2010-11-01

12

Amino acids  

MedlinePLUS

Amino acids are organic compounds that combine to form proteins . Amino acids and proteins are the building blocks of life. When proteins are digested or broken down, amino acids are left. The human body uses amino acids ...

13

Amino acid transport in Lactobacillus helveticus  

Microsoft Academic Search

Amino acid transport in Lactobacillus helveticus was analyzed. Strain specificity of amino acid transport was speculated between L. helveticus NCDO2712 and SBT2171. Glucose energized L. helveticus NCDO2712 actively transported and accumulated the essential and growth stimulating amino acids (leucine, isoleucine, valine, threonine, lysine, aspartic acid, glutamic acid, tyrosine, arginine, and histidine). Uptake of proline, phenylalanine and tryptophan was not observed.

Hadjime Nakajima; Edmund R. S. Kunji; Bert Poolman; Wil N. Konings

1998-01-01

14

Design and Synthesis of Human ABCB1 (P-Glycoprotein) Inhibitors by Peptide Coupling of Diverse Chemical Scaffolds on Carboxyl and Amino Termini of (S)-Valine-Derived Thiazole Amino Acid.  

PubMed

P-glycoprotein (P-gp) serves as a therapeutic target for the development of multidrug resistance reversal agents. In this study, we synthesized 21 novel compounds by peptide coupling at corresponding carboxyl and amino termini of (S)-valine-based bis-thiazole and monothiazole derivatives with diverse chemical scaffolds. Using calcein-AM efflux assay, we identified compound 28 (IC50 = 1.0 ?M) carrying 3,4,5-trimethoxybenzoyl and 2-aminobenzophenone groups, respectively, at the amino and carboxyl termini of the monothiazole zwitter-ion. Compound 28 inhibited the photolabeling of P-gp with [(125)I]-iodoarylazidoprazosin with IC50 = 0.75 ?M and stimulated the basal ATP hydrolysis of P-gp in a concentration-dependent manner (EC50 ATPase = 0.027 ?M). Compound 28 at 3 ?M reduced resistance in cytotoxicity assay to paclitaxel in P-gp-expressing SW620/Ad300 and HEK/ABCB1 cell lines. Biochemical and docking studies showed site-1 to be the preferable binding site for 28 within the drug-binding pocket of human P-gp. PMID:24773054

Singh, Satyakam; Prasad, Nagarajan Rajendra; Chufan, Eduardo E; Patel, Bhargav A; Wang, Yi-Jun; Chen, Zhe-Sheng; Ambudkar, Suresh V; Talele, Tanaji T

2014-05-22

15

BranchedChain Amino Acids  

Microsoft Academic Search

The branched-chain amino acids (BCAAs) leucine, isoleucine, and valine are synthesized by bacteria,\\u000a fungi, and plants, but are essential for vertebrates including humans, who must receive them from their\\u000a diet. The interest to construct overproducing industrial strains therefore stems from the need to supplement\\u000a the food or feed with these amino acids to use them in medical treatment and as

Miroslav Pátek

16

Effect of L-Valine on the growth and characterization of Sodium Acid Phthalate (SAP) single crystals  

NASA Astrophysics Data System (ADS)

Undoped and amino acid doped good quality single crystals of Sodium Acid Phthalate crystals (SAP) were grown by slow evaporation solution growth technique which are semiorganic in nature. The effect of amino acid (L-Valine) dopant on the growth and the properties of SAP single crystal was investigated. The single crystal X-ray diffraction studies and FT-IR studies were carried out to identify the crystal structure and the presence of functional groups in undoped and L-Valine doped SAP crystals. The transparent nature of the grown crystal was observed using UV-Visible spectrum. The thermal decomposition of the doped SAP crystals was investigated by thermo gravimetric analysis (TGA) and differential thermal analysis (DTA). The enhancement in the NLO property of the undoped and L-Valine doped SAP crystals using KDP crystal as a reference was studied using SHG measurements. Vickers micro hardness measurements are used for the study of mechanical strength of the grown crystals.

Nirmala, L. Ruby; Prakash, J. Thomas Joseph

2013-06-01

17

Amino Acids  

NSDL National Science Digital Library

The Featured Molecules this month are the 20 standard α-amino acids found in proteins and serve as background to the paper by Barone and Schmidt on the Nonfood Applications of Proteinaceous Renewable Materials. The molecules are presented in two formats, the neutral form and the ionized form found in solution at physiologic pH.

18

NRPSs and amide ligases producing homopoly(amino acid)s and homooligo(amino acid)s.  

PubMed

Microorganisms are capable of producing a wide variety of biopolymers. Homopoly(amino acid)s and homooligo(amino acid)s, which are made up of only a single type of amino acid, are relatively rare; in fact, only two homopoly(amino acid)s have been known to occur in nature: poly(?-L-lysine) (?-PL) and poly(?-glutamic acid) (?-PGA). Bacterial enzymes that produce homooligo(amino acid)s, such as L-?-lysine-, L-valine-, L-leucine-, L-isoleucine-, L-methionine-, and L-glutamic acid-oligopeptides and poly(?-l-glutamic acid) (?-PGA) have recently been identified, as well as ?-PL synthetase and ?-PGA synthetase. This article reviews the current knowledge about these unique enzymes producing homopoly(amino acid)s and homooligo(amino acid)s. PMID:23817633

Hamano, Yoshimitsu; Arai, Toshinobu; Ashiuchi, Makoto; Kino, Kuniki

2013-08-01

19

Plasma amino acids  

MedlinePLUS

Plasma amino acids is a screening test done on infants that looks at the amounts of amino ... Rheumatoid arthritis High or low concentrations of individual plasma amino acids must be interpreted along with other ...

20

Prebiotic Synthesis of Hydrophobic and Protein Amino Acids  

Microsoft Academic Search

The formation of amino acids by the action of electric discharges on a mixture of methane, nitrogen, and water with traces of ammonia was studied in detail. The presence of glycine, alanine, alpha -amino-n-butyric acid, alpha -aminoisobutyric acid, valine, norvaline, isovaline, leucine, isoleucine, alloisoleucine, norleucine, proline, aspartic acid, glutamic acid, serine, threonine, allothreonine, alpha -hydroxy-gamma -aminobutyric acid, and alpha ,gamma

David Ring; Yecheskel Wolman; Nadav Friedmann; Stanley L. Miller

1972-01-01

21

Providing a diet deficient in valine but with excess leucine results in a rapid decrease in feed intake and modifies the postprandial plasma amino acid and ?-keto acid concentrations in pigs.  

PubMed

Indispensable AA are involved in the control of feed intake. When a diet deficient in Val is offered to pigs, feed intake is typically reduced. This effect is aggravated when dietary Leu is supplied in excess of the requirement. If an unbalanced supply of branched-chain AA (BCAA) is harmful, an anorectic response may serve as a mechanism to prevent this situation. We verified this hypothesis by measuring the voluntary feed intake of a balanced diet offered during the 30-min period 1 h after ingestion of a test meal deficient or not in Val (Val- and Val+) with an excess of Leu. Twelve and four 6-wk-old crossbred female pigs were used in Exp. 1 and 2, respectively. Prior ingestion of the Val- test meal resulted in a 14% reduction in feed intake compared with that observed after ingestion of the Val+ test meal (P = 0.06) in Exp. 1, indicating that the signal to reduce feed intake occurred within 1 h. It is possible that the plasma concentration of the limiting AA serves as a signal for the dietary AA deficiency. We therefore determined the postprandial plasma concentrations of BCAA and their ?-keto acids after ingestion of Val- and Val+ in 4 pigs in Exp. 2. After ingestion of the Val- diet, plasma concentrations of Val and its keto acid were reduced compared with values observed after ingestion of the Val+ diet. The peak concentration occurred earlier after ingestion of the Val- diet compared with that of the Val+ diet. Although the plasma concentration increased after the meal, it declined rapidly in pigs offered Val-, and the Val concentration 4 h after ingestion of the meal was even less than that observed in the fasted state. In conclusion, it appears that the pig is able to detect a deficient supply of Val within 1 h after ingestion. The plasma concentration of Val or its concentration relative to the other BCAA during the postprandial period may act as a signal indicating the AA deficiency. PMID:22585822

Gloaguen, M; Le Floc'h, N; Corrent, E; Primot, Y; van Milgen, J

2012-09-01

22

Branched-Chain Amino and Keto Acid Biochemistry and Cellular Biology in Central Nervous System Diseases.  

National Technical Information Service (NTIS)

Branched-chain amino acids (BCAAs: leucine, isoleucine, and valine) are essential components of many biochemical and biological processes. There are well-established pathways, such as fatty acid synthesis and oxidation, anabolic use to synthesize new prot...

J. Henriques

2009-01-01

23

of natural amino acids  

Microsoft Academic Search

A new method for the synthesis of protected N a -(ø-Y-alkyl) amino acids (Y is a thio, amino or carboxy group) and related compounds by reductive alkylation of natural amino acids is reported. These new amino acids serve as building units for the synthesis of backbone-cyclic peptides. They are orthogonally protected at the Æ-amino position by butoxycarbonyl (Boc) or 9-fluorenylmethoxycarbonyl

Gal Bitan; Dan Muller; Ron Kasher; Evgenia V. Gluhov; Chaim Gilon

1997-01-01

24

Prebiotic Synthesis of Hydrophobic and Protein Amino Acids  

PubMed Central

The formation of amino acids by the action of electric discharges on a mixture of methane, nitrogen, and water with traces of ammonia was studied in detail. The presence of glycine, alanine, ?-amino-n-butyric acid, ?-aminoisobutyric acid, valine, norvaline, isovaline, leucine, isoleucine, alloisoleucine, norleucine, proline, aspartic acid, glutamic acid, serine, threonine, allothreonine, ?-hydroxy-?-aminobutyric acid, and ?,?-diaminobutyric acid was confirmed by ion-exchange chromatography and gas chromatography-mass spectrometry. All of the primary ?-amino acids found in the Murchison Meteorite have been synthesized by this electric discharge experiment.

Ring, David; Wolman, Yecheskel; Friedmann, Nadav; Miller, Stanley L.

1972-01-01

25

Amino acid analysis  

NASA Technical Reports Server (NTRS)

The process and apparatus for qualitative and quantitative analysis of the amino acid content of a biological sample are presented. The sample is deposited on a cation exchange resin and then is washed with suitable solvents. The amino acids and various cations and organic material with a basic function remain on the resin. The resin is eluted with an acid eluant, and the eluate containing the amino acids is transferred to a reaction vessel where the eluant is removed. Final analysis of the purified acylated amino acid esters is accomplished by gas-liquid chromatographic techniques.

Winitz, M.; Graff, J. (inventors)

1974-01-01

26

Mechanism of specific influence of L-Glutamic acid on the shape of L-Valine crystals  

NASA Astrophysics Data System (ADS)

The specific interaction between L-valine (L-Val) and L-glutamic acid (L-Glu) in the process of evaporative crystallization from an aqueous solution has been investigated. It was found that only 2.0% (wt/wt) of L-Glu against the total amount of L-Val was required to induce significant agglomeration of L-Val. Interestingly, the agglomeration was only induced under acidic conditions, suggesting that the electrostatic interaction was an effective factor for the agglomeration process. As well as the electrostatic interaction, the length of the amino acid side chain was identified as another important factor. In addition, we confirmed that the incorporation rate of L-Glu into L-Val crystals was different during the nucleation and crystal growth stages. Based on these results, a mechanism has been proposed for the interaction of L-Glu and L-Val during the agglomeration process.

Yoshiura, Hiromu; Nagano, Hiroshi; Hirasawa, Izumi

2013-01-01

27

Effects of running the Bostom Marathon on plasma concentrations of large neutral amino acids  

NASA Technical Reports Server (NTRS)

Plasma large neutral amino acid concentrations were measured in thirty-seven subjects before and after completing the Boston Marathon. Concentrations of tyrosine, phenylalanine, and methionine increased, as did their 'plasma ratios' (i.e., the ratio of each amino acid's concentration to the summed plasma concentrations of the other large neutral amino acids which compete with it for brain uptake). No changes were noted in the plasma concentrations of tryptophan, leucine, isoleucine, nor valine; however, the 'plasma ratios' of valine, leucine, and isoleucine all decreased. These changes in plasma amino acid patterns may influence neurotransmitter synthesis.

Conlay, L. A.; Wurtman, R. J.; Lopez G-Coviella, I.; Blusztajn, J. K.; Vacanti, C. A.; Logue, M.; During, M.; Caballero, B.; Maher, T. J.; Evoniuk, G.

1989-01-01

28

Amino Acid Transport by the Filamentous Fungus Arthrobotrys conoides1  

PubMed Central

Uptake of l-valine by germinated spores of Arthrobotrys conoides has all the characteristics of a system of transport that requires an expenditure of energy by the cells. It is dependent on temperature and has an energy of activation of 16,000 cal/mole. Uptake is optimal at pH 5 to 6. l-Valine accumulated against a concentration gradient and is not lost from the cells by leakage or exchange. The process requires energy supplied by the metabolic reactions that are inhibited by catalytic amounts of 2,4-dinitrophenol and azide. The kinetics of the system are consistent with a mechanism of transport that depends on a limited number of sites on the cell surface, and the Michaelis constant for the system is 1.5 × 10?5 to 7.5 × 10?5m. Modification of the amino or carboxyl group abolishes l-valine uptake. The process is competitively inhibited by d-valine, glycine, and other neutral amino acids (Ki = 1.5 × 10?5 to 4.0 × 10?5m), indicating a lack of stereospecificity, and also indicating that aliphatic side chain is not required for binding with the carrier. The transport system has less affinity for acidic amino acids (glutamic and aspartic acids) than neutral amino acids, and a greater affinity for basic amino acids (histidine, lysine, and arginine). The range of affinity is in the order of 100, as measured in terms of Ki values for various compounds. The data presented provide suggestive evidence that the uptake by A. conoides of all amino acids except proline is mediated by a single carrier system that possesses an overall negative charge.

Gupta, Rishab K.; Pramer, David

1970-01-01

29

Amino Acids and Chirality  

NASA Technical Reports Server (NTRS)

Amino acids are among the most heavily studied organic compound class in carbonaceous chondrites. The abundance, distributions, enantiomeric compositions, and stable isotopic ratios of amino acids have been determined in carbonaceous chondrites fi'om a range of classes and petrographic types, with interesting correlations observed between these properties and the class and typc of the chondritcs. In particular, isomeric distributions appear to correlate with parent bodies (chondrite class). In addition, certain chiral amino acids are found in enantiomeric excess in some chondrites. The delivery of these enantiomeric excesses to the early Earth may have contributed to the origin of the homochirality that is central to life on Earth today. This talk will explore the amino acids in carbonaceous chondritcs and their relevance to the origin of life.

Cook, Jamie E.

2012-01-01

30

[Overproduction of noncanonical amino acids by Escherichia coli cells].  

PubMed

Overproduction of noncanonical amino acids norvaline and norleucine by Escherichia coli with inactivated acetohydroxy acid synthases was demonstrated. The cultivation conditions for the overproduction of noncanonical amino acids were studied. The effect of the restoration of acetohydroxy acid synthase activity, increased expression of the leuABCD operon, and inactivation of the biosynthetic threonine deaminase on norvaline and norleucine synthesis was studied. When grown under valine limitation, E. coli cells with inactivated acetohydroxy acid synthases and an elevated level of expression of the valine operon were shown to accumulate norvaline and norleucine (up to 0.8 and 4 g/l, respectively). These results confirm the existing hypothesis of norvaline and norleucine formation from 2-ketobutyrate by leucine biosynthesis enzymes. PMID:18297871

Sycheva, E V; Iampol'skaia, T A; Preobrazhenskaia, E S; Novikova, A E; Matrosov, N G; Sto?nova, N V

2007-01-01

31

2-amino-3-(oxirane-2,3-dicarboxamido)-propanoyl-valine, an effective peptide antibiotic from the epiphyte Pantoea agglomerans 48b/90.  

PubMed

The epiphyte Pantoea agglomerans 48b/90, which has been isolated from soybean leaves, belongs to the Enterobacteriaceae, as does the plant pathogen Erwinia amylovora, which causes fire blight on rosaceous plants such as apples and leads to severe economic losses. Since P. agglomerans efficiently antagonizes phytopathogenic bacteria, the P. agglomerans strain C9-1 is used as a biocontrol agent (BlightBan C9-1). Here we describe the bioassay-guided isolation of a peptide antibiotic that is highly active against the plant pathogen E. amylovora and pathovars of Pseudomonas syringae, and we elucidate its structure. Bioassay-guided fractionation using anion-exchange chromatography followed by hydrophobic interaction liquid chromatography yielded the bioactive, highly polar antibiotic. The compound was identified as 2-amino-3-(oxirane-2,3-dicarboxamido)-propanoyl-valine by using high-resolution electrospray ionization mass spectrometry and nuclear magnetic resonance techniques. This peptide was found to be produced by three of the nine P. agglomerans strains analyzed. Notably, the biocontrol strain P. agglomerans C9-1 also produces 2-amino-3-(oxirane-2,3-dicarboxamido)-propanoyl-valine. Previously, 2-amino-3-(oxirane-2,3-dicarboxamido)-propanoyl-valine has been characterized only from Serratia plymuthica. 2-Amino-3-(oxirane-2,3-dicarboxamido)-propanoyl-valine has been shown to inhibit the growth of the human pathogen Candida albicans efficiently, but its involvement in the defense of epiphytes against phytopathogenic bacteria has not been investigated so far. PMID:19820144

Sammer, Ulrike F; Völksch, Beate; Möllmann, Ute; Schmidtke, Michaela; Spiteller, Peter; Spiteller, Michael; Spiteller, Dieter

2009-12-01

32

Formation of Meteoritic Amino Acids: Isovaline and its Isomers  

NASA Astrophysics Data System (ADS)

It has been known for several decades that amino acids, and other complex organics, are found in meteorites. In particular, Murchison (CM) samples contain over seventy amino acids, these being identified by high-level chromatographic methods. Among Murchison's amino acids, isovaline stands out as being both non-biological (non-protein) and having a relatively high abundance. While approximately equal amounts of D- and L- isovaline have been reported in Murchison and other CM meteorites, this molecule's structure appears to prohibit its racemization in aqueous solutions. We recently have investigated the low-temperature solid-phase chemistry of both isovaline and valine with an eye toward each molecule's formation, stability, and possible interconversions of their D and L enantiomers. Ion-irradiated isovalineand valine-containing ices were examined by IR spectroscopy and highly-sensitive liquid chromatography/time-of-flight mass spectral methods to assess both amino-acid destruction and racemization. Samples were studied in the presence and in the absence of water-ice, and the destruction of both isovaline and valine was measured as a function of radiation dose. In addition, we have synthesized isovaline, valine, and their amino acid isomers by solid-phase radiation-chemical pathways other than the oft-invoked Strecker process. This presentation will review and summarize some of our recent findings and place them in a context of related work. - Our work has been supported by a grant to the Goddard Center for Astrobiology through the NASA Astrobiology Institute. Experiments were performed in the Cosmic Ice Laboratory (RLH, MHM) and the Astrobiology Analytical Laboratory (JPD) at the NASA Goddard Space Flight Center.

Hudson, Reggie; Moore, Marla; Dworkin, Jason

33

Subcritical Water Extraction of Amino Acids from Atacama Desert Soils  

NASA Technical Reports Server (NTRS)

Amino acids are considered organic molecular indicators in the search for extant and extinct life in the Solar System. Extraction of these molecules from a particulate solid matrix, such as Martian regolith, will be critical to their in situ detection and analysis. The goals of this study were to optimize a laboratory amino acid extraction protocol by quantitatively measuring the yields of extracted amino acids as a function of liquid water temperature and sample extraction time and to compare the results to the standard HCl vapor- phase hydrolysis yields for the same soil samples. Soil samples from the Yungay region of the Atacama Desert ( Martian regolith analog) were collected during a field study in the summer of 2005. The amino acids ( alanine, aspartic acid, glutamic acid, glycine, serine, and valine) chosen for analysis were present in the samples at concentrations of 1 - 70 parts- per- billion. Subcritical water extraction efficiency was examined over the temperature range of 30 - 325 degrees C, at pressures of 17.2 or 20.0 MPa, and for water- sample contact equilibration times of 0 - 30 min. None of the amino acids were extracted in detectable amounts at 30 degrees C ( at 17.2 MPa), suggesting that amino acids are too strongly bound by the soil matrix to be extracted at such a low temperature. Between 150 degrees C and 250 degrees C ( at 17.2 MPa), the extraction efficiencies of glycine, alanine, and valine were observed to increase with increasing water temperature, consistent with higher solubility at higher temperatures, perhaps due to the decreasing dielectric constant of water. Amino acids were not detected in extracts collected at 325 degrees C ( at 20.0 MPa), probably due to amino acid decomposition at this temperature. The optimal subcritical water extraction conditions for these amino acids from Atacama Desert soils were achieved at 200 degrees C, 17.2 MPa, and a water- sample contact equilibration time of 10 min.

Amashukeli, Xenia; Pelletier, Christine C.; Kirby, James P.; Grunthaner, Frank J.

2007-01-01

34

Amino acid analysis.  

PubMed

Amino acid analysis (AAA) is one of the best methods to quantify peptides and proteins. Two general approaches to quantitative AAA exist, namely, classical postcolumn derivatization following ion-exchange chromatography and precolumn derivatization followed by reversed-phase HPLC (RP-HPLC). Excellent instrumentation and several specific methodologies are available for both approaches, and both have advantages and disadvantages. This unit focuses on picomole-level AAA of peptides and proteins using the most popular precolumn-derivatization method, namely, phenylthiocarbamyl amino acid analysis (PTC-AAA). It is directed primarily toward those interested in establishing the technology with a modest budget. PTC derivatization and analysis conditions are described, and support and alternate protocols describe additional techniques necessary or useful for most any AAA method--e.g., sample preparation, hydrolysis, instrument calibration, data interpretation, and analysis of difficult or unusual residues such as cysteine, tryptophan, phosphoamino acids, and hydroxyproline. PMID:18429107

Crabb, J W; West, K A; Dodson, W S; Hulmes, J D

2001-05-01

35

Preparation and physical properties of some C 18 unsaturated fatty esters containing L -amino acid residues and methyl esters of N -stearoylamino acids  

Microsoft Academic Search

A series of five C18 unsaturated fatty esters (1–5) containing anL-amino acid residue (glycine, alanine, valine, leucine, phenylalanine) was prepared from methyl 12-amino-9-cis-octadecenoate and five methylN-stearoyl-amino acid ester derivatives (6–10) from stearoyl chloride and the sameL-amino acids. The infrared analysis of compounds 1–5 showed characteristic absorption bands at 3300 and 1665 cm?1 for the amino and amido functions, while the

Marcel S. F. Lie Ken Jie; H. B. Lao; David W. Y. Leung

1990-01-01

36

Abiotic formation of valine peptides under conditions of high temperature and high pressure.  

PubMed

We investigated the oligomerization of solid valine and the stabilities of valine and valine peptides under conditions of high temperature (150-200 °C) and high pressure (50-150 MPa). Experiments were performed under non-aqueous condition in order to promote dehydration reaction. After prolonged exposure of monomeric valine to elevated temperatures and pressures, the products were analyzed by liquid chromatography mass spectrometry comparing their retention times and masses. We identified linear peptides that ranged in size from dimer to hexamer, as well as a cyclic dimer. Previous studies that attempted abiotic oligomerization of valine in the absence of a catalyst have never reported valine peptides larger than a dimer. Increased reaction temperature increased the dissociative decomposition of valine and valine peptides to products such as glycine, ?-alanine, ammonia, and amines by processes such as deamination, decarboxylation, and cracking. The amount of residual valine and peptide yields was greater at higher pressures at a given temperature, pressure, and reaction time. This suggests that dissociative decomposition of valine and valine peptides is reduced by pressure. Our findings are relevant to the investigation of diagenetic processes in prebiotic marine sediments where similar pressures occur under water-poor conditions. These findings also suggest that amino acids, such as valine, could have been polymerized to peptides in deep prebiotic marine sediments within a few hundred million years. PMID:22915229

Furukawa, Yoshihiro; Otake, Tsubasa; Ishiguro, Takato; Nakazawa, Hiromoto; Kakegawa, Takeshi

2012-12-01

37

A valine-resistant mutant of Arabidopsis thaliana displays an acetolactate synthase with altered feedback control  

Microsoft Academic Search

A valine-resistant mutant line, VAL-2, ofArabidopsis thaliana (L.) Heynh. was identified by screening M 2 populations of ethylmethane-sulfonate-mutagenized seeds. The resistance was found to be due to a single, dominant, nuclear gene mutation. Assay of acetolactate synthase (ALS) indicated that the valine resistance in this mutant is caused by decreased sensitivity of ALS to the branched-chain amino acids, valine, leucine

K. Wu; G. Mourad; J. King

1994-01-01

38

A valine-resistant mutant of Arabidopsis thaliana displays an acetolactate synthase with altered feedback control  

Microsoft Academic Search

A valine-resistant mutant line, VAL-2, of Arabidopsis thaliana (L.) Heynh. was identified by screening M 2 populations of ethylmethane-sulfonate-mutagenized seeds. The resistance was found to be due to a single, dominant, nuclear gene mutation. Assay of acetolactate synthase (ALS) indicated that the valine resistance in this mutant is caused by decreased sensitivity of ALS to the branched-chain amino acids, valine,

K. Wu; G. Mourad; J. King

1994-01-01

39

Redox behavior of Re(V)-amino acid containing complexes.  

PubMed

Three cationic complexes containing the [Re((V))O](3+) core (general formula [ReO(dien-H)(aa)](+), dien=diethylenetriamine, aa=glycine, alanine, valine) were studied on polycrystalline Au electrodes employing cyclic voltammetry techniques. The electrochemical behavior of the amino acids (aa) was also evaluated. Experiments were performed at pH 7.0 aqueous solutions at room temperature. The voltammogram of the complex showed current contributions related to the [Re((VI))O](4+)/[Re((V))O](3+) redox couple, the counterion, and the amino acid ligand. PMID:16290610

Cerdá, M Fernanda; Méndez, Eduardo; Malacrida, Leonel; Zinola, Carlos F; Melián, Cecilia; Martins, M Elisa; Castro Luna, Ana M; Kremer, Carlos

2002-05-15

40

Use of Diphenyliodonium Bromide in the Synthesis of Some N-Phenyl ?-Amino Acids  

Microsoft Academic Search

The N-phenyl methyl esters 4 of glycine, alanine, valine, leucine, isoleucine, phenylalanine, methionine, proline, serine, threonine, tyrosine, aspartic acid, and glutamic acid have been synthesized in good to excellent yields using diphenyliodonium bromide, AgNO3, and a catalytic amount of CuBr starting from the relevant amino acid ester. The chiral integrity of the amino acids 5 was maintained during these reactions,

Jason D. McKerrow; Jasim M. A. Al-Rawi; Peter Brooks

2010-01-01

41

Identification of a novel system L amino acid transporter structurally distinct from heterodimeric amino acid transporters.  

PubMed

A cDNA that encodes a novel Na+-independent neutral amino acid transporter was isolated from FLC4 human hepatocarcinoma cells by expression cloning. When expressed in Xenopus oocytes, the encoded protein designated LAT3 (L-type amino acid transporter 3) transported neutral amino acids such as l-leucine, l-isoleucine, l-valine, and l-phenylalanine. The LAT3-mediated transport was Na+-independent and inhibited by 2-aminobicyclo[2.2.1]heptane-2-carboxylic acid, consistent with the properties of system L. Distinct from already known system L transporters LAT1 and LAT2, which form heterodimeric complex with 4F2 heavy chain, LAT3 was functional by itself in Xenopus oocytes. The deduced amino acid sequence of LAT3 was identical to the gene product of POV1 reported as a prostate cancer-up-regulated gene whose function was not determined, whereas it did not exhibit significant similarity to already identified transporters. The Eadie-Hofstee plots of LAT3-mediated transport were curvilinear, whereas the low affinity component is predominant at physiological plasma amino acid concentration. In addition to amino acid substrates, LAT3 recognized amino acid alcohols. The transport of l-leucine was electroneutral and mediated by a facilitated diffusion. In contrast, l-leucinol, l-valinol, and l-phenylalaninol, which have a net positive charge induced inward currents under voltage clamp, suggesting these compounds are transported by LAT3. LAT3-mediated transport was inhibited by the pretreatment with N-ethylmaleimide, consistent with the property of system L2 originally characterized in hepatocyte primary culture. Based on the substrate selectivity, affinity, and N-ethylmaleimide sensitivity, LAT3 is proposed to be a transporter subserving system L2. LAT3 should denote a new family of organic solute transporters. PMID:12930836

Babu, Ellappan; Kanai, Yoshikatsu; Chairoungdua, Arthit; Kim, Do Kyung; Iribe, Yuji; Tangtrongsup, Sahatchai; Jutabha, Promsuk; Li, Yuewei; Ahmed, Nesar; Sakamoto, Shinichi; Anzai, Naohiko; Nagamori, Seishi; Endou, Hitoshi

2003-10-31

42

Amino acids in Arctic aerosols  

NASA Astrophysics Data System (ADS)

Amino acids are significant components of atmospheric aerosols, affecting organic nitrogen input to marine ecosystems, atmospheric radiation balance, and the global water cycle. The wide range of amino acid reactivities suggest that amino acids may serve as markers of atmospheric transport and deposition of particles. Despite this potential, few measurements have been conducted in remote areas to assess amino acid concentrations and potential sources. Polar regions offer a unique opportunity to investigate atmospheric processes and to conduct source apportionment studies of such compounds. In order to better understand the importance of amino acid compounds in the global atmosphere, we determined free amino acids (FAAs) in seventeen size-segregated aerosol samples collected in a polar station in the Svalbard Islands from 19 April until 14 September 2010. We used an HPLC coupled with a tandem mass spectrometer (ESI-MS/MS) to analyze 20 amino acids and quantify compounds at fmol m-3 levels. Mean total FAA concentration was 1070 fmol m-3 where serine and glycine were the most abundant compounds in almost all samples and accounted for 45-60% of the total amino acid relative abundance. The other eighteen compounds had average concentrations between 0.3 and 98 fmol m-3. The higher amino acid concentrations were present in the ultrafine aerosol fraction (< 0.49 ?m) and accounted for the majority of the total amino acid content. Local marine sources dominate the boreal summer amino acid concentrations, with the exception of the regional input from Icelandic volcanic emissions.

Scalabrin, E.; Zangrando, R.; Barbaro, E.; Kehrwald, N. M.; Gabrieli, J.; Barbante, C.; Gambaro, A.

2012-11-01

43

Amino acids in Arctic aerosols  

NASA Astrophysics Data System (ADS)

Amino acids are significant components of atmospheric aerosols, affecting organic nitrogen input to marine ecosystems, atmospheric radiation balance, and the global water cycle. The wide range of amino acid reactivities suggest that amino acids may serve as markers of atmospheric transport and deposition of particles. Despite this potential, few measurements have been conducted in remote areas to assess amino acid concentrations and potential sources. Polar regions offer a unique opportunity to investigate atmospheric processes and to conduct source apportionment studies of such compounds. In order to better understand the importance of amino acid compounds in the global atmosphere, we determined free amino acids (FAAs) in seventeen size-segregated aerosol samples collected in a polar station in the Svalbard Islands from 19 April until 14 September 2010. We used an HPLC coupled with a tandem mass spectrometer (ESI-MS/MS) to analyze 20 amino acids to quantify compounds at fmol m-3 levels. Mean total FAA concentration was 1070 fmol m-3 where serine and glycine were the most abundant compounds in almost all samples and accounted for 45-60% of the total amino acid relative abundance. The other eighteen compounds had average concentrations between 0.3 and 98 fmol m-3. The higher amino acid concentrations were present in the ultrafine aerosol fraction (<0.49 ?m) and accounted for the majority of the total amino acid content. Local marine sources dominate the boreal summer amino acid concentrations, with the exception of the regional input from Icelandic volcanics.

Scalabrin, E.; Zangrando, R.; Barbaro, E.; Kehrwald, N. M.; Gabrieli, J.; Barbante, C.; Gambaro, A.

2012-07-01

44

Comparative Genomics of Regulation of Fatty Acid and BranchedChain Amino Acid Utilization in Proteobacteria  

Microsoft Academic Search

Bacteria can use branched-chain amino acids (ILV, i.e., isoleucine, leucine, valine) and fatty acids (FAs) as sole carbon and energy sources converting ILV into acetyl-coenzyme A (CoA), propanoyl-CoA, and propionyl- CoA, respectively. In this work, we used the comparative genomic approach to identify candidate transcrip- tional factors and DNA motifs that control ILV and FA utilization pathways in proteobacteria. The

Alexey E. Kazakov; Dmitry A. Rodionov; Eric Alm; Adam Paul Arkin; Inna Dubchak; Mikhail S. Gelfand

2009-01-01

45

[Bioavailability of amino acids in beans (Phaseolus vulgaris)].  

PubMed

Biological availability of amino acids of three common bean (Phaseolus vulgaris) varieties was evaluated in four, healthy adult subjects, consuming bean-based diets by the amino acid absorption technique and the short-term nitrogen balance method. The amino acid composition was determined according to the ionic interchange method, and tryptophan was estimated by a colorimetric procedure. The essential amino acid (EAA) and non-essential amino acid (NEAA) pattern suggests that no significant differences in content exists in the three bean varieties. When the EAA patterns were compared with those of FAO/WHO, the limiting AA in decreasing order were found to be: tryptophan, valine and threonine (sulfur AA are not considered because the hydrolysis used in this study destroys them); and the AA surpassing the reference pattern were the aromatic AA and isoleucine. Apparent (AD) and true (TD) digestibilities of the EAA fluctuated between 33 and 59% and 60 and 85%, respectively, for black beans. With red beans, these results diminished: 29 and 55% AD and 64 and 81% TD, while for white beans the limits extended: 18 and 57% AD and 36 and 86% TD. Valine proved to be the EAA of lower biological availability, and lysine and phenylalanine the most available. It is suggested that the low digestibility of valine could be due to the amino acid imbalance existing in the bean protein, since this contains an excess of isoleucine and leucine in relation to valine. The AD and TD of the AAE with respect to the NEAA were of 0.89 and 0.98 for black bean, 0.89 and 0.96 for the red and 0.77 and 0.90 for the white, which indicates that biological availability of the NEAA is higher than that of the EAA. Findings thus confirm that biological determination of the TD of protein permits prediction of the TD of the AA, since a positive correlation (r = 0.93) statistically significant was found (p less than 0.05) among them. Utilization of the TD parameter instead of that of AD to estimate the protein quality is therefore recommended. PMID:1822068

Blanco, A; Bressani, R

1991-03-01

46

Preferential Treatment: Interaction Between Amino Acids and Minerals  

NASA Astrophysics Data System (ADS)

Amino acids are the building blocks of proteins and are important for some models of the origin of life. Polymerization of amino acids from dilute solution is unlikely without a scaffold or catalyst. The surfaces of early Earth minerals are the most likely candidates for this role. The surface adsorption behavior of 12 amino acids (L-alanine, L-serine, L-aspartic acid, L-proline, L- phenylalanine, L-valine, L-arginine, d-amino valeric acid, glycine, L-lysine, L-isoleucine, and B-alanine) on 21 minerals (quartz, calcite, enstatite, illite, olivine, pyrrhotite, pyrite, alkali basalt, albite, analcime, chlorite, barite, hydroxyl apatite, hematite, magnetite, aluminum hydroxide, kaolin, silica gel, corundum, rutile, and montmorillonite) was determined via batch adsorption experiments. Absorption was determined for concentrations between 10-4M and 10-6M in the presence of 0.1M NaCl, and between pH values of 3 and 9 at 25 degrees C. The equilibrated solutions were centrifuged, filtered, derivatized using a fluorescent amino group tag (dansyl-chloride) and analyzed by HPLC. Adsorption was standardized using BET surface area measurements for each mineral to give the number of mols of each amino acid adsorbed per square meter for each mineral. The results indicate an enormous difference in the adsorption of amino acids between minerals, along with major differences in the adsorption of individual amino acids on the same mineral surface. There is also a change in the absorbance of amino acids as the pH changes. Many previous studies of amino acid concentration and catalysis by minerals have used clay minerals because of their high surface areas, however, this data suggests that the surfaces of minerals such as calcite, quartz and pyrite have even higher affinities for amino acids. The results suggest mineral surfaces that could be optimal locations for the polymerization of molecules linked to the origin of life.

Crapster-Pregont, E. J.; Cleaves, H. J.; Hazen, R. M.

2008-12-01

47

Piezoelectricity in protein amino acids  

NASA Astrophysics Data System (ADS)

The piezoelectric activity of protein amino acids and their compounds has been measured using the pulse method at a frequency of 10 MHz. It has been established that, at room temperature, the piezoelectric effect is not observed in ?-glycine (achiral amino acid) and protein amino acids of the L modification, namely, methionine, phenylalanine, and tryptophan. An assumption has been made that this phenomenon is associated with the enhanced damping of elastic vibrations excited in samples due to the piezoelectric effect.

Lemanov, V. V.; Popov, S. N.; Pankova, G. A.

2011-06-01

48

Chromatographic resolution of racemic ?-amino acids: chiral stationary phase derived from modified xanthan gum.  

PubMed

Enantiomeric resolution of ?-amino acids into L-amino acid and D-amino acid via column chromatography using chiral stationary phase was performed. For this purpose, a dynamic chiral stationary phase prepared by grafting of methylmethacrylate onto xanthan gum (XG) was successfully employed in resolving various ?-amino acids racemates. The peculiarities of the chromatographic behaviour of xanthan gum-graft-poly(methylmethacrylate)-amino acid interaction and the mechanism of their retention in column are discussed. The enantioselective properties of the xanthan gum-graft-poly(methylmethacrylate) in the separation of enantiomers of ?-amino acids were studied using acidic solution of alanine, leucine, valine and tryptophan. The procedure is characterized by simplicity, efficiency and relatively low cost to analyze enantiomers of some amino acids. PMID:23399277

Pandey, Sadanand; Mishra, Shivani B

2013-02-15

49

Determination of the n-terminal amino acid sequence of mengbean leghemoglobin  

Microsoft Academic Search

Four components of mungbean [ Vigna radiata (L.) Wilzeck] leghemoglobin (Lb) were identified and their N-terminal amino acid sequences were determined. The four components (Lb1, Lb2, Lb3, and Lb4) which differed in their isoelectric point are considered to be the products of at least two different genes. They have valine as the N-terminal amino acid residue which is a distinct

Danilo M. Mendoza; Satoshi Mori; Mitsuo Chino

1993-01-01

50

Alteration of substrate specificity of fructosyl-amino acid oxidase from Fusarium oxysporum  

Microsoft Academic Search

Fructosyl-amino acid oxidase (FOD-F) from Fusarium oxysporum f. sp. raphani (NBRC 9972) is the enzyme catalyzing the oxidative deglycation of fructosyl-amino acids such as $$ N^{\\\\varepsilon }$$-fructosyl $$ N^{\\\\alpha }$$-benzyloxycarbonyl-lysine (FZK) and fructosyl valine (FV), which are model compounds of the glycated proteins in blood. Wild-type\\u000a FOD-F has high activities toward both substrates. We obtained a mutant FOD-F, which reacts

Maki Fujiwara; Jun-ichi Sumitani; Shinji Koga; Issei Yoshioka; Takuji Kouzuma; Shigeyuki Imamura; Takashi Kawaguchi; Motoo Arai

2007-01-01

51

Differences in the Ability of Lactic Streptococci to Form Aldehydes from Certain Amino Acids  

Microsoft Academic Search

SUMMARY Resting cells of five cultures of lactic streptococci were examined as to their ability to form flavorful aldehydes from four amino acids. Two strains of Streptococcus cremoris~ two strains of Streptococcus tactis, and one strain of Streptococcus lactis ear. maltigenes were incubated with isoleucine, valine, methionine, and phenylalanine, and the resulting aldehydes were isolated and identified as their 2,4-dinitrophenylhydrazones.

Patricia Mac Leod; M. E. Morgan

1958-01-01

52

Asymmetric amplification in amino acid sublimation involving racemic compound to conglomerate conversion.  

PubMed

A straightforward unprecedented sublimation protocol that reveals both conversion of a racemic compound into a racemic conglomerate and subsequent enantioenrichment has been developed for the proteinogenic amino acid valine. The phenomenon has been observed in closed and open systems, providing insight into asymmetric amplification mechanisms under presumably prebiotic conditions. PMID:21109890

Viedma, Cristóbal; Noorduin, Wim L; Ortiz, José E; de Torres, Trinidad; Cintas, Pedro

2011-01-14

53

Predictive value of tryptophan\\/large neutral amino acids ratio to antidepressant response  

Microsoft Academic Search

The molar ratio of total plasma tryptophan to the sum of other large neutral amino acids (viz., valine, isoleucine, leucine, tyrosine, phenylalanine), thought to reflect brain serotonin formation, was estimated in 69 patients with major depression before and after 1 week of treatment with different serotonin reuptake inhibitors, fluvoxamine (n = 28), fluoxetine (n = 10), citalopram (n = 7),

Valentina Lucini; Adelio Lucca; Marco Catalano; Enrico Smeraldi

1996-01-01

54

Amino acids as natural inhibitors for hydrate formation in CO2 sequestration.  

PubMed

The motivation for this work was the potential of hydrophobic amino acids such as glycine, l-alanine, and l-valine to be applied as thermodynamic hydrate inhibitors (THIs). To confirm their capabilities in inhibiting the formation of gas hydrates, three-phase (liquid-hydrate-vapor) equilibrium conditions for carbon dioxide hydrate formation in the presence of 0.1-3.0 mol % amino acid solutions were determined in the range of 273.05-281.45 K and 14.1-35.2 bar. From quantitative analyses, the inhibiting effects of the amino acids (on a mole concentration basis) decreased in the following order: l-valine > l-alanine > glycine. The application of amino acids as THIs has several potential advantages over conventional methods. First, the environmentally friendly nature of amino acids as compared to conventional inhibitors means that damage to ecological systems and the environment could be minimized. Second, the loss of amino acids in recovery process would be considerably reduced because amino acids are nonvolatile. Third, amino acids have great potential as a model system in which to investigate the inhibition mechanism on the molecular level, since the structure and chemical properties of amino acids are well understood. PMID:21663046

Sa, Jeong-Hoon; Lee, Bo Ram; Park, Da-Hye; Han, Kunwoo; Chun, Hee Dong; Lee, Kun-Hong

2011-07-01

55

Parasite sulphur amino acid metabolism  

Microsoft Academic Search

This paper reviews current knowledge regarding the metabolism of the sulphur-containing amino acids methionine and cysteine in parasitic protozoa and helminths. Particular emphasis is placed on the unusual aspects of parasite biochemistry which may present targets for rational design of anti-parasite drugs. In general, the basic pathways of sulphur amino acid metabolism in most parasites resemble those of their mammalian

John Walker; John Barrett

1997-01-01

56

Amino acids in carbonaceous chondrites.  

PubMed

For almost 20 years laboratory experiments have advanced the concepts of chemical evolution, particularly with regard to formation of the amino acids. What has been generally lacking is concrete natural evidence for this chemical evolution hypothesis. The recent development of sophisticated analytical techniques and availability of carbonaceous chondrites with a minimum of terrestrial contamination has resulted in the identification of amino acids which provide strong evidence for a natural extraterrestrial chemical synthesis. Since the initial find in the Murchison meteorite (a type II carbonaceous chondrite) of both protein and nonprotein amino acids with nearly equal abundances of D and L isomers, further studies have been carried out. These studies have revealed the presence of at least 35 amino acids; the population consists of a wide variety of linear, cyclic and polyfunctional amino acids which shows a trend of decreasing concentration with increasing carbon number. Investigations of the Murray meteorite (a type II carbonaceous chondrite) has produced similar results, but studies of the Orgueil meteorite (a type I carbonaceous chondrite) show only a limited suite of amino acids, some of which appear to be indigenous while others appear to be terrestrial contaminanats. A sample of the Murchison meteorite was extracted with D2O and in addition of 'free' amino acids, showing no deuterium incorporation, some amino acids showed the presence of deuterium suggesting either a 'precursor(s)' or hydrogen-deuterium exchange which require(s) formation of carbon-hydrogen bonds. PMID:1153189

Lawless, J G; Peterson, E

1975-01-01

57

Solvent Effects on the Protonation Constants of Some ? Amino Acid Esters in 1,4Dioxane–Water Mixtures  

Microsoft Academic Search

The stoichiometric protonation constants of some ?-amino acid esters (glycine methyl ester, glycine t-butyl ester, l-valine methyl ester, l-valine ethyl ester, l-valine t-butyl ester, l-serine methyl ester, l-serine ethyl ester, l-leucine methyl ester, l-leucine ethyl ester, l-leucine t-butyl ester, l-alanine methyl ester, l-alanine benzyl ester, l-phenylalanine methyl ester, l-phenylalanine ethyl ester, and l-phenylalanine t-butyl ester) in water and 20%, 40%,

Alev Do?an; Nazife Aslan; Esin Canel; Esma K?l?ç

2010-01-01

58

Growth Response of Nitrosomonas europaea to Amino Acids  

PubMed Central

Growth responses of Nitrosomonas europaea to individual amino acids or vitamins was observed in log-phase cultures, as was the incorporation of carbon-14 labeled amino acids. Nitrite formation and protein synthesis were increased by l-glutamic acid, l-aspartic acid, l-serine, and l-glutamine. l-Lysine, l-histidine, l-threonine, l-valine, l-methionine, and l-arginine were inhibitory. The other amino acids had no effect on growth. All of the uniformly labeled amino acids added at low concentrations were taken up by growing cells and distributed into cell fractions. From 1 to 12% of the added radioactivity was present in cells analyzed in late log phase, depending on the amino acid; glycine and l-serine caused accumulation of the label to the greatest extent, whereas l-aspartic and l-glutamic acids were among those incorporated to the least extent. Aspartic acid increased both cell protein and nitrite values, but did not alter the ratio of protein to nitrite from that found in controls.

Clark, Connie; Schmidt, E. L.

1967-01-01

59

Free amino acid profiling in the giant puffball mushroom (Calvatia gigantea) using UPLC-MS/MS.  

PubMed

Wild edible and medicinal mushroom, Calvatia gigantea, was quantitatively analyzed for the determination of its free amino acids using ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). The concentrations of total free amino acids, essential and non-essential amino acids were 199.65mg/100g, 113.69mg/100g, and 85.96mg/100g in C. gigantea, respectively. This study showed that C. gigantea, so called a giant puffball mushroom, has free amino acids content. The essential amino acids: tryptophan, isoleucine, valine, phenylalanine, leucine, threonine, lysine, histidine, methionine, and the non-essential amino acids: tyrosine, 4-hyrdroxy proline, arginine, proline, glycine, serine, alanine, glutamine, glutamic acid, aspargine, aspartic acid were detected. PMID:24731318

K?vrak, Ibrahim; K?vrak, Seyda; Harmandar, Mansur

2014-09-01

60

The relationship between the biosynthetic paths to the amino acids and their coding  

NASA Astrophysics Data System (ADS)

The genetic code could not have been fixed until the means for biosynthesis of the amino acids was at hand. The biosynthetic enzymes could not be optimized until the genetic code ceased to be rearranged. Therefore the development of the code and the development of the biosynthesis of the amino acids occurred concurrently. The present day biosynthetic pathways of amino acids, examined from this point of view, help to explain the present set of coded amino acids, in particular the absence of norvaline, norleucine, homoserine, ornithine, and alpha-aminobutyric acid. An order of development of biosyntheses is also proposed. Lysine was first, followed by valine and isoleucine. The more common primordial amino acids did not need biosyntheses so early. The central pathways of metabolism probably developed in response to a need for amino acid biosynthesis.

McClendon, John H.

1987-09-01

61

Raman spectra of amino acids and their aqueous solutions  

NASA Astrophysics Data System (ADS)

Amino acids are the basic "building blocks" that combine to form proteins and play an important physiological role in all life-forms. Amino acids can be used as models for the examination of the importance of intermolecular bonding in life processes. Raman spectra serve to obtain information regarding molecular conformation, giving valuable insights into the topology of more complex molecules (peptides and proteins). In this paper, amino acids and their aqueous solution have been studied by Raman spectroscopy. Comparisons of certain values for these frequencies in amino acids and their aqueous solutions are given. Spectra of solids when compared to those of the solute in solution are invariably much more complex and almost always sharper. We present a collection of Raman spectra of 18 kinds of amino acids ( L-alanine, L-arginine, L-aspartic acid, cystine, L-glutamic acid, L-glycine, L-histidine, L-isoluecine, L-leucine, L-lysine, L-phenylalanine, L-methionone, L-proline, L-serine, L-threonine, L-tryptophan, L-tyrosine, L-valine) and their aqueous solutions that can serve as references for the interpretation of Raman spectra of proteins and biological materials.

Zhu, Guangyong; Zhu, Xian; Fan, Qi; Wan, Xueliang

2011-03-01

62

Molar extinction coefficients in aqueous solutions of some amino acids  

Microsoft Academic Search

Mass attenuation coefficients of amino acids viz. glycine (C2H5NO2), l-Serine (C3H7NO3), l-Theronine (C4H9NO3), l-Proline (C5H9NO2), l-Valine (C5H11NO2) and l-Phenylalanine (C9H11NO2) in aqueous solutions have been determined at 81, 356, 511, 662, 1173 and 1332 keV by the gamma-ray transmission method in a narrow beam good geometry setup. Precisely measured densities of these solutions were used for the determination of these

Kulwant Singh; G. K. Sandhu; Gagandeep Kaur; B. S. Lark

2002-01-01

63

Amino Acids from a Comet  

NASA Technical Reports Server (NTRS)

NASA's Stardust spacecraft returned samples from comet 81P/Wild 2 to Earth in January 2006. Examinations of the organic compounds in cometary samples can reveal information about the prebiotic organic inventory present on the early Earth and within the early Solar System, which may have contributed to the origin of life. Preliminary studies of Stardust material revealed the presence of a suite of organic compounds including several amines and amino acids, but the origin of these compounds (cometary- vs. terrestrial contamination) could not be identified. We have recently measured the carbon isotopic ratios of these amino acids to determine their origin, leading to the first detection of a coetary amino acid.

Cook, Jamie Elisla

2009-01-01

64

Regulation of valine and. alpha. -ketoisocaproate metabolism in rat kidney mitochondria  

SciTech Connect

Activities of branched-chain amino acid (BCAA) aminotransferase (BCAT) and {alpha}-keto acid dehydrogenase (BCKD) were assayed in mitochondria isolated from kidneys of rats. Rates of transamination of valine and oxidation of keto acids {alpha}-ketoisocaproate (KIC) or {alpha}-ketoisovalerate (KIV) were estimated using radioactive tracers of the appropriate substrate from amounts of {sup 14}C-labeled products formed. Because of the high mitochondrial BCAT activity, an amino acceptor for BCAT, {alpha}-ketoglutarate ({alpha}-KG) or KIC, was added to the assay medium when valine was the substrate. Rates of valine transamination and subsequent oxidation of the KIV formed were determined with 0.5 mM {alpha}-KG as the amino acceptor; these rates were 5- to 50-fold those without added {alpha}-KG. Rates of CO{sub 2} evolution from valine also increased when KIC was present; however, with KIC concentrations above 0.2 mM, rates of CO{sub 2} evolution from valine declined although rates of transamination continued to rise. When 0.05 mM KIC was added to the assay medium, oxidation of KIC was suppressed by inclusion of valine or glutamate in the medium. When valine was present KIC was not oxidized preferentially, presumably because it was also serving as an amino acceptor for BCAT. These results indicate that as the supply of amino acceptor, {alpha}-KG or KIC, is increased in mitochondria not only is the rate of valine transamination stimulated but also the rate of oxidation of the KIV formed from valine. Thus the rate of oxidation of BCAA can be controlled by factors that influence the rate and direction of BCAA transamination and, thereby, the supply of substrate for BCKD.

Miller, R.H.; Harper, A.E. (Univ. of Wisconsin, Madison (USA))

1988-10-01

65

Pseudo-poly(amino acid)s: study on construction and characterization of novel chiral and thermally stable nanostructured poly(ester-imide)s containing different trimellitylimido-amino acid-based diacids and pyromellitoyl-tyrosine-based diol  

Microsoft Academic Search

A new class of chiral and potentially biodegradable poly(ester-imide)s (PEI)s as pseudo-poly(amino acid)s (PAA)s bearing natural\\u000a amino acids in the main chain was synthesized. In this investigation, N,N?-(pyromellitoyl)-bis-(L-tyrosine dimethyl ester) as a biodegradable optically active diphenol and synthesized trimellitic\\u000a anhydride-derived dicarboxylic acids containing different natural amino acids such as S-valine, L-methionine, L-leucine, L-isoleucine,\\u000a and L-phenylalanine were used for direct polyesterification.

Shadpour Mallakpour; Fatemeh Zeraatpisheh

2011-01-01

66

Prevention of incorporation of non-standard amino acids into protein  

US Patent & Trademark Office Database

The instant invention is drawn to the methods and compositions necessary to provide recombinant proteins with a substantially reduced or eliminated content of norleucine or other non-standard amino acids. Various embodiments of the invention provide for the substantial elimination of the incorporation of non-standard amino acids into recombinant proteins by the co-expression or enhanced expression of a protein (or the enzymatically active portion thereof) capable of degrading norleucine or other non-standard amino acids, including norvaline, beta-methylnorleucine, and homoisoleucine. In certain particular embodiments of the invention, the norleucine is degraded by a glutamate dehydrogenase, a leucine dehydrogenase, a valine dehydrogenase, a phenylalanine dehydrogenase, a glutamate/leucine/phenylalanine/valine dehydrogenase, or an opine dehydrogenase. Also provided are the cells and DNA constructs for carrying out these methods.

2013-12-10

67

Amino acid transport in podocytes.  

PubMed

It has recently been shown that formation of podocyte foot processes is dependent on a constant source of lipids and proteins (Simons M, Saffrich R, Reiser J, and Mundel P. J Am Soc Nephrol 10: 1633-1639, 1999). Here we characterize amino acid transport mechanisms in differentiated cultured podocytes and investigate whether it may be disturbed during podocyte injury. RT-PCR studies detected mRNA for transporters of neutral amino acids (ASCT1, ASCT2, and B(0/+)), cationic AA (CAT1 and CAT3), and anionic AA (EAAT2 and EAAT3). Alanine (Ala), asparagine, cysteine (Cys), glutamine (Gln), glycine (Gly), leucine (Leu), methionine (Met), phenylalanine (Phe), proline (Pro), serine (Ser), threonine (Thr), glutamic acid (Glu), arginine (Arg), and histidine (His) depolarized podocytes and increased their whole cell conductances. Depletion of extracellular Na(+) completely inhibited the depolarization induced by Ala, Gln, Glu, Gly, Leu, and Pro and decreased the depolarization induced by Arg and His, indicating the presence of Na(+)-dependent amino acid transport. Incubation of podocytes with 100 microg/ml puromycin aminonucleoside for 24 h significantly attenuated the effects induced by the various amino acids by approximately 70%. The data indicate the existence of different amino acid transporter systems in podocytes. Alteration of amino acid transport may participate in podocyte injury and disturbed foot process formation. PMID:10836988

Gloy, J; Reitinger, S; Fischer, K G; Schreiber, R; Boucherot, A; Kunzelmann, K; Mundel, P; Pavenstädt, H

2000-06-01

68

Electrochemical and XPS studies of decylamides of ?-amino acids adsorption on carbon steel in acidic environment  

NASA Astrophysics Data System (ADS)

Corrosion inhibition of steel in hydrochloric acid by decylamides of ?-amino acids derivatives was studied using gravimetric and electrochemical techniques. Protection efficiencies of 90% were obtained with 100 ppm of tyrosine and glycine derivatives, while alanine and valine derivatives reached only 80%. The order of increasing inhibition efficiency was correlated with the modification of the molecular structure of inhibitors. Potentiodynamic polarization curves indicated that both the decylamide of tyrosine and glycine acted primarily as anodic type inhibitors, whereas the decylamide of alanine and valine were of the cathodic type. Thermodynamic parameters and Flory-Huggins adsorption isotherms described the experimental findings. The number of active sites, equilibrium constant, enthalpy and change of free energy were computed for all inhibitors studied. This information suggested that organic molecules were adsorbed and displaced water molecules from the steel surface. X-ray photoelectron spectroscopy confirmed that species of N, C and O interacted with steel to form a continuous protective film.

Olivares, O.; Likhanova, N. V.; Gómez, B.; Navarrete, J.; Llanos-Serrano, M. E.; Arce, E.; Hallen, J. M.

2006-02-01

69

Amino Acids and the Mitochondria  

Microsoft Academic Search

\\u000a This chapter describes some of the important physiological functions of amino acids in the mitochondria and the alterations\\u000a caused by specific pathologies. To some extent all of the featured items are dependent upon the movement of amino acids across\\u000a the highly selective permeability barrier that is the inner mitochondrial membrane. The performance of this transport by specific\\u000a carriers is the

Nicola King

70

Industrial production of amino acids by coryneform bacteria.  

PubMed

In the 1950s Corynebacterium glutamicum was found to be a very efficient producer of L-glutamic acid. Since this time biotechnological processes with bacteria of the species Corynebacterium developed to be among the most important in terms of tonnage and economical value. L-Glutamic acid and L-lysine are bulk products nowadays. L-Valine, L-isoleucine, L-threonine, L-aspartic acid and L-alanine are among other amino acids produced by Corynebacteria. Applications range from feed to food and pharmaceutical products. The growing market for amino acids produced with Corynebacteria led to significant improvements in bioprocess and downstream technology as well as in molecular biology. During the last decade big efforts were made to increase the productivity and to decrease the production costs. This review gives an overview of the world market for amino acids produced by Corynebacteria. Significant improvements in bioprocess technology, i.e. repeated fed batch or continuous production are summarised. Bioprocess technology itself was improved furthermore by application of more sophisticated feeding and automatisation strategies. Even though several amino acids developed towards commodities in the last decade, side aspects of the production process like sterility or detection of contaminants still have increasing relevance. Finally one focus of this review is on recent developments in downstream technology. PMID:12948636

Hermann, Thomas

2003-09-01

71

Cyclo(valine-valine) inhibits Vibrio cholerae virulence gene expression.  

PubMed

Vibrio cholerae has been shown to produce a cyclic dipeptide, cyclo(phenylalanine-proline) (cFP), that functions to repress virulence factor production. The objective of this study was to determine if heterologous cyclic dipeptides could repress V. cholerae virulence factor production. To that end, three synthetic cyclic dipeptides that differed in their side chains from cFP were assayed for virulence inhibitory activity in V. cholerae. The results revealed that cyclo(valine-valine) (cVV) inhibited virulence factor production by a ToxR-dependent process that resulted in the repression of the virulence regulator aphA. cVV-dependent repression of aphA was found to be independent of known aphA regulatory genes. The results demonstrated that V. cholerae was able to respond to exogenous cyclic dipeptides and implicated the hydrophobic amino acid side chains on both arms of the cyclo dipeptide scaffold as structural requirements for inhibitory activity. The results further suggest that cyclic dipeptides have potential as therapeutics for cholera treatment. PMID:24644247

Vikram, Amit; Ante, Vanessa M; Bina, X Renee; Zhu, Qin; Liu, Xinyu; Bina, James E

2014-06-01

72

Energy absorption and exposure buildup factors of essential amino acids.  

PubMed

The effective atomic number and effective electron density in amino acids are of significant interest due to their use in various applications. The energy absorption buildup factors, exposure buildup factors, effective atomic numbers, and electron densities of essential amino acids such as Leucine (C6H13NO2), Lysine (C6H14N2O2), Methionine (C5H11NO2S), Phenylalanine (C9H11NO2), Threonine (C4H9NO3), Tryptophan (C11H12N2O2), Valine (C5H11NO2), Arginine (C6H14N4O2), and Histidine (C6H9N3O2) were determined theoretically in the energy range 0.015-15?MeV. PMID:24605325

Bursal?o?lu, Ertu?rul; Balkan, Begüm; Kavanoz, H Birtan; Okutan, Mustafa; ?çelli, Orhan; Yalç?n, Zeynel

2014-01-01

73

Excretion of amino acids by humans during space flight  

NASA Technical Reports Server (NTRS)

We measured the urine amino acid distribution patterns before, during and after space flight on the Space Shuttle. The urine samples were collected on two separate flights of the space shuttle. The first flight lasted 9.5 days and the second flight 15 days. Urine was collected continuously on 8 subjects for the period beginning 10 d before launch to 6 d after landing. Results: In contrast to the earlier Skylab missions where a pronounced amino aciduria was found, on shuttle the urinary amino acids showed little change with spaceflight except for a marked decrease in all of the amino acids on FD (flight day) 1 (p<0.05) and a reduction in isoleucine and valine on FD3 and FD4 (p<0.05). Conclusions: (i) Amino aciduria is not an inevitable consequence of space flight. (ii) The occurrence of amino aciduria, like muscle protein breakdown is a mission specific effect rather than part of the general human response to microgravity.

Stein, T. P.; Schluter, M. D.

1998-01-01

74

Investigation of 60Co ?-irradiated L-(-) malic acid, N-methyl- DL-valine and L-glutamic acid ?-ethyl ester by electron paramagnetic resonance technique  

NASA Astrophysics Data System (ADS)

The electron paramagnetic resonance spectra of ?-irradiated L-(-) malic acid, N-methyl- DL-valine and L-glutamic acid ?-ethyl ester powders have been investigation at room temperature. Radiation damage centres are attributed to HOOCCH 2?HCOOH, (CH 3) 2?CH(NHCH 3)COOH and C 2H 5OCOCH 2CH 2?(NH 2)COOH radicals, respectively. The spectra have been computer simulated. The EPR parameters of the observed radicals have been determined and discussed.

Ba?kan, M. Halim; Ayd?n, Murat; Osmano?lu, ?emsettin

75

Bacterial ABC transporters of amino acids  

Microsoft Academic Search

There are two subfamilies of ABC uptake systems for amino acids in bacteria, the polar amino acid transport family and the hydrophobic amino acid transport family. We consider the general properties of these families and we examine the specific transporters. Focusing on some of the best-studied ATP binding cassette transporters we also examine the mechanism of amino acid uptake, paying

Arthur H. F. Hosie; Philip S. Poole

2001-01-01

76

Chiral changes of simple amino acids in early Earth's ocean by meteorite impacts: Experimental simulations  

NASA Astrophysics Data System (ADS)

It has been recognized that meteorite impacts on early Earth ocean may have contributed significantly for molecules related to the origin of life to originate and evolve. We have already established the formation of simple biomolecules from inorganic materials through oceanic impacts that may have occurred at late heavy bombardment. These simple molecules including amino acids need to be subjected to further developments to initiate life on the Earth. The chirality of terrestrial amino acids constructing proteins is only L-type. In order to make clear the the point that biomolecules are formed by oceanic impacts of meteorites, it wll be crucial to determine how they select the chirality. In order to investigate the basic chemistry on chirality of simple amino acids, we tried to simulate experimentally the chiral change of some amino acids present in ocean at that time under shock loading. Each aqueous solution (0.1 M) of L- and D-valine was prepared and used as mixtures of olivine powders and solutions in sealed steel containers. We performed shock recovery experiments at an impact condition where samples were compressed at ~5 GPa. The analytical results of shock recovered solutions indicate that valine survives significantly (~10%) and that L- and D-valines transform partially to D- and L-valine, respectively. The transformation rate varied with the chemical species present in solutions. These results imply that meteorite impacts as well as the surrounding conditions play important roles to control the chirality of simple amino acids that may have been formed at that time.

Takase, A.; Sekine, T.; Furukawa, Y.; Kakegawa, T.

2012-12-01

77

Assessment of the relevance of the antibiotic 2-amino-3-(oxirane-2,3-dicarboxamido)-propanoyl-valine from Pantoea agglomerans biological control strains against bacterial plant pathogens.  

PubMed

The epiphyte Pantoea agglomerans 48b/90 (Pa48b) is a promising biocontrol strain against economically important bacterial pathogens such as Erwinia amylovora. Strain Pa48b produces the broad-spectrum antibiotic 2-amino-3-(oxirane-2,3-dicarboxamido)-propanoyl-valine (APV) in a temperature-dependent manner. An APV-negative mutant still suppressed the E. amylovora population and fire blight disease symptoms in apple blossom experiments under greenhouse conditions, but was inferior to the Pa48b wild-type indicating the influence of APV in the antagonism. In plant experiments with the soybean pathogen Pseudomonas syringae pv. glycinea both, Pa48b and the APV-negative mutant, successfully suppressed the pathogen. Our results demonstrate that the P. agglomerans strain Pa48b is an efficient biocontrol organism against plant pathogens, and we prove its ability for fast colonization of plant surfaces over a wide temperature range. PMID:23233458

Sammer, Ulrike F; Reiher, Katharina; Spiteller, Dieter; Wensing, Annette; Völksch, Beate

2012-12-01

78

Expression in Lactococcus lactis of functional genes related to amino acid catabolism and cheese aroma formation is influenced by branched chain amino acids.  

PubMed

Formation of cheese aroma compounds by Lactococcus lactis from amino acid catabolism depends on a complex network of reactions, which involve enzymes such as aminotransferases, dehydrogenases, lyases, and decarboxylases, among others. Based on the ability of some L. lactis strains to grow with low requirements of amino acids, we have studied in L. lactis IFPL730 the effect of the branched chain amino acid (BCAA) content on the expression of functional genes related to amino acid catabolism and aroma compound formation (araT, bcaT, kivD, ytjE and panE). L. lactis IFPL730 growth rate decreased under leucine, valine or isoleucine starvation but the strain reached similar viable counts at the stationary phase in all culture conditions studied. The level of expression of some genes encoding enzymes involved in amino acid catabolism changed significantly (P<0.05) when those conditions were compared. Specially, ?-ketoisovalerate decarboxylase (kivD), BCAA-specific aminotransferase (bcaT) and C-S lyase (yjtE) gene expressions increased markedly by both isoleucine and valine starvation. In addition to gene expression, formation of volatile compounds was determined in all growth conditions. The results showed that BCAA starvation conditions caused a significant increase (P<0.05) in the formation of metabolic end products related to cheese aroma, such as 3-methylbutanal and 3-methylbutanol. PMID:23107499

García-Cayuela, Tomás; Gómez de Cadiñanos, Luz P; Peláez, Carmen; Requena, Teresa

2012-10-15

79

Amino acid losses during hemodialysis with infusion of amino acids and glucose  

Microsoft Academic Search

Amino acid losses during hemodialysis with infusion of amino acids and glucose. This study evaluated the effects during hemodialysis of intravenous infusion of amino acids and glucose on plasma amino acid and glucose concentrations and amino acid losses. Eight men undergoing maintenance hemodialysis were each studied during two dialyses using glucose-free dialysate. During one hemodialysis, they were infused with 800

Marsha Wolfson; Michael R Jones; Joel D Kopple

1982-01-01

80

THE SPECIFIC AMINO ACID REQUIREMENTS OF A HUMAN CARCINOMA CELL (STRAIN HELA) IN TISSUE CULTURE  

PubMed Central

The amino acid requirements of a human uterine carcinoma cell (HeLa strain) have been defined. The 12 compounds previously found to be essential for the growth of a mouse fibroblast proved similarly essential for this human epithelial cell. They included arginine, cyst(e)ine, histidine, and tyrosine, in addition to the eight amino acids required for nitrogen balance in man (isoleucine, leucine, lysine, methionine, phenylalanine, threonine, tryptophan, and valine). Only the L-amino acids were active; the D-enantiomorphs had no demonstrable effect at physiologic concentrations. The minimum concentrations required for survival and limited growth varied from 0.003 µM per ml. for L-tryptophan, to 0.1 µM per ml. for L-lysine. The concentrations permitting optimum growth similarly varied from 0.01 µM per ml. for tryptophan, to 0.1 µM per ml. for leucine, isoleucine, threonine, lysine, and valine. The latter optimum concentrations of the individual amino acids were closely correlated with their serum levels. With at least six of the amino acids, high concentrations, in the range 1 to 10 µM per ml., caused a definite growth inhibition. In the absence of a single essential amino acid, degenerative changes occurred in the cells, culminating in their death and dissolution. In the early stages, however, these degenerative changes could be reversed by the restoration of the missing component.

Eagle, Harry

1955-01-01

81

Regulation of isoleucine-valine biosynthesis in Saccharomyces cerevisiae.  

PubMed

The threonine deaminase gene (ILV1) of Saccharomyces cerevisiae has been designated "multifunctional" since Bollon (1974) indicated its involvement both in the catalysis of the first step in isoleucine biosynthesis and in the regulation of the isoleucine-valine pathway. Its role in regulation is characterized by a decrease in the activity of the five isoleucine-valine enzymes when cells are grown in the presence of the three branched-chain amino acids, isoleucine, valine and leucine (multivalent repression). We have demonstrated that the regulation of AHA reductoisomerase (encoded by ILV5) and branched-chain amino acid transaminase is unaffected by the deletion of ILV1, subsequently revealing that the two enzymes can be regulated in the absence of threonine deaminase. Both threonine deaminase activity and ILV1 mRNA levels increase in mutants (gcd2 and gcd3) having constitutively depressed levels of enzymes under the general control of amino acid biosynthesis, as well as in response to starvation for tryptophan and branched-chain amino acid imbalance. Thus, the ILV1 gene is under general amino acid control, as is the case for both the ILV5 and the transaminase gene. Multivalent repression of reductoisomerase and transaminase can be observed in mutants defective in general control (gcn and gcd), whereas this is not the case for threonine deaminase. Our analysis suggests that repression effected by general control is not complete in minimal medium. Amino acid dependent regulation of threonine deaminase is only through general control, while the branched-chain amino acid repression of AHA reducto isomerase and the transaminase is caused both by general control and an amino acid-specific regulation. PMID:3289762

Holmberg, S; Petersen, J G

1988-03-01

82

Effect of whey protein on plasma amino acids in diabetic mice  

PubMed Central

The aim of this study was to investigate the effect of whey protein on plasma amino acid levels in a mouse model of type II diabetes, using high-performance liquid chromatography (HPLC). The composition and content of amino acids in the whey proteins were analyzed using HPLC. Type I and type II diabetic mouse models were prepared using streptozotocin (STZ) and normal mice were used as a control. The ICR mice in each group were then randomly divided into four subgroups, to which 0, 10, 20 and 40% whey protein, respectively, was administered for four weeks. Changes in the plasma amino acid levels were observed in each group. The proportions of leucine, isoleucine and valine in the whey proteins were 14.40, 5.93 and 5.32% of the total amino acids, respectively, that is, the branched-chain amino acid content was 25.65%. The levels of branched-chain amino acids increased in the plasma of the normal and model mice following the administration of whey proteins by gavage and the amino acid levels increased as the concentration of the administered protein increased. In addition, the branched-chain amino acid levels in the blood of the model mice were higher than those in the normal mice. The levels of plasma amino acids in diabetic mice increased following gavage with whey protein, which is rich in branched-chain amino acids.

HAN, TING; CAI, DONGLIAN; GENG, SHANSHAN; WANG, YING; ZHEN, HUI; WU, PEIYING

2013-01-01

83

A novel family of (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids - analogues of ?-amino acids.  

PubMed

A series of novel (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids - analogues of proteinogenic and nonproteinogenic ?-amino acids were prepared. The synthetic methodology was based on nucleophilic addition of (trifluoromethyl)phosphinic acid or (difluoromethyl)phosphinic acid or its ethyl ester to substrates with C=N or activated C=C double bonds. Analogues of glycine, phenylglycine, alanine, valine, proline, aminomalonic and aspartic acids were thus prepared. Three-component one-pot reactions of (trifluoromethyl)phosphinic acid and dibenzylamine with aldehydes were also tested to prepare the title compounds. PMID:24778725

Pavlenko, Natalia V; Oos, Tatiana I; Yagupolskii, Yurii L; Gerus, Igor I; Doeller, Uwe; Willms, Lothar

2014-01-01

84

Signalling by amino acid nutrients.  

PubMed

It is clear that mTORC1 (mammalian target of rapamycin complex 1) is regulated by the presence of ambient amino acid nutrients. However, the mechanism by which amino acids regulate mTORC1 is still open to question, despite extensive efforts. Our recent work has revealed that PR61?, a B56 family regulatory subunit of PP2A (protein phosphatase 2A), associates with and regulates the activity of MAP4K3 (mitogen-activated protein kinase kinase kinase kinase 3), a protein kinase regulated by amino acid sufficiency that acts upstream of mTORC1. In searching for a physiological process regulated by amino acids, we have demonstrated recently that arginine plays a role in the activation of LPS (lipopolysaccharide)-induced MEK [MAPK (mitogen-activated protein kinase)/ERK (extracellular-signal-regulated kinase) kinase]/ERK signalling in macrophages. PP2A similarly associates with the upstream regulator of MEK in this signalling pathway, TPL-2 (tumour progression locus-2), in response to arginine availability. Thus PP2A is a negative regulator of both MAP4K3 and TPL-2 in both mTORC1 and MEK/ERK signalling pathways. PMID:21428916

Yan, Lijun; Lamb, Richard F

2011-04-01

85

Amino acid metabolism in ruminants  

Microsoft Academic Search

All animals require amino acids (AA) which are the building blocks of proteins required for optimal growth, reproduction, lactation, and maintenance. In ruminants, proteins and AA are first subject to microbial degradation in the rumen making it difficult to predict the quality and quantity of AA that are absorbed by the animal. In ruminants, absorbed AA comes from microbial protein

Limin Kung; Lyle M. Rode

1996-01-01

86

Biosynthesis of natural products containing ?-amino acids.  

PubMed

Covering: up to January, 2014We focus here on ?-amino acids as components of complex natural products because the presence of ?-amino acids produces structural diversity in natural products and provides characteristic architectures beyond those of ordinary ?-l-amino acids, thus generating significant and unique biological functions in nature. In this review, we first survey the known bioactive ?-amino acid-containing natural products including nonribosomal peptides, macrolactam polyketides, and nucleoside-?-amino acid hybrids. Next, the biosynthetic enzymes that form ?-amino acids from ?-amino acids and the de novo synthesis of ?-amino acids are summarized. Then, the mechanisms of ?-amino acid incorporation into natural products are reviewed. Because it is anticipated that the rational swapping of the ?-amino acid moieties with various side chains and stereochemistries by biosynthetic engineering should lead to the creation of novel architectures and bioactive compounds, the accumulation of knowledge regarding ?-amino acid-containing natural product biosynthetic machinery could have a significant impact in this field. In addition, genome mining of characteristic ?-amino acid biosynthetic genes and unique ?-amino acid incorporation machinery could lead to the discovery of new ?-amino acid-containing natural products. PMID:24926851

Kudo, Fumitaka; Miyanaga, Akimasa; Eguchi, Tadashi

2014-07-01

87

Carbon-11-labeled amino acids for the rectilinear and positron tomographic imaging of the human pancreas.  

PubMed

Modification of the Bücherer-Strecker amino acid synthesis facilitated the production of DL-[11C]tryptophan and DL-[11C]valine for clinical trials in patients with proven or suspected pancreatic disease. Examples of rectilinear scans and tomographic images of the pancreas are presented in this initial paper. Positron computed tomography was done with the ORTEC ECAT system. Rapid localization of these C-11-labeled amino acids and fast clearance from the plasma permit almost immediate examination following i.v. injection. Illustrative images include the normal pancreas, pancreatitis, and pancreatic carcinoma. The use of positron tomobraphy with C-11-labeled DL-tryptophan and DL-valine appears to offer a new and promising diagnostic modality for the detection and study of pancreatic diseases. PMID:317098

Hübner, K F; Andrews, G A; Buonocore, E; Hayes, R L; Washburn, L C; Collmann, I R; Gibbs, W D

1979-06-01

88

Facile synthesis of multiamino vinyl poly(amino acid)s for promising bioapplications.  

PubMed

We presented a general and facile strategy to prepare biocompatible multiamino polymers. Series of new monomers were synthesized by esterification of 2-hydroxyethyl methacrylate (HEMA) and Boc-amino acids, such as Boc-l-phenylalanine, Boc-glycine, Boc-l-alanine, Boc-l-valine, and Boc-l-lysine. Subsequent vinyl polymerization of monomers gave rise to vinyl poly(amino acid)s with a side primary amino group at each unit if deprotected. Both atom transfer radical polymerization (ATRP) and conventional free radical polymerization (FRP) were employed to prepare the multiamino polymers. A well controlled effect upon molecular weight with the standard first-order kinetics was achieved in cases of ATRP, and high molecular weight polymers were obtained via FRP. MTT assay showed that cell survival rates for the multiamino polymers were almost maintained above 90% and that their cytotoxicities were much lower than that of linear PEI (PEI 25000). Zeta potential measurements demonstrated that the vinyl poly(amino acid)s are electropositive, and AFM measurements showed that the vinyl poly(amino acid)s could tightly condense DNA into granular structures at a suitable concentration. The combination of facile availability, controlled productivity, low cytotoxicity and strong binding ability with DNA promises the great potential of the novel multiamino polymers in bioapplications. PMID:21114313

Sun, Haiyan; Gao, Chao

2010-12-13

89

Acetohydroxy acid synthase I, a required enzyme for isoleucine and valine biosynthesis in Escherichia coli K-12 during growth on acetate as the sole carbon source.  

PubMed Central

Escherichia coli K-12 has two acetohydroxy acid synthase (AHAS) isozymes (AHAS I and AHAS III). Both of these isozymes catalyze the synthesis of alpha-aceto-alpha-hydroxybutyrate and alpha-acetolactate, which are key intermediates of the isoleucine-valine biosynthetic pathway. Strains lacking either isozyme but not both activities have been previously shown to grow well in minimal media in the absence of isoleucine and valine on any of several commonly used carbon sources (e.g., glucose or succinate). We report the characterization of mutants that were unable to grow on either acetate or oleate as a sole carbon source due to a defect in isoleucine-valine biosynthesis. The defect in isoleucine-valine biosynthesis was expressed only on these carbon sources and was due to the loss of AHAS I activity, resulting from lesions in the ilvBN operon. Previously identified ilvBN mutant strains also failed to grow on acetate or oleate minimal media. Our results indicated that AHAS I is an essential enzyme for isoleucine and valine biosynthesis when E. coli K-12 is grown on acetate or oleate as the sole carbon source. AHAS III was expressed during growth on acetate or oleate but was somehow unable to produce sufficient amounts of alpha-aceto-alpha-hydroxybutyrate and alpha-acetolactate to allow growth.

Dailey, F E; Cronan, J E

1986-01-01

90

When and why amino acids?  

PubMed Central

This article reviews especially the early history of glutamate and GABA as neurotransmitters in vertebrates. The proposal that some amino acids could mediate synaptic transmission in the CNS initially met with much resistance. Both GABA and its parent glutamate are abundant in the brain; but, unlike glutamate, GABA had no obvious metabolic function. By the late 1950s, the switch of interest from electrical to chemical transmission invigorated the search for central transmitters. Its identification with Factor I, a brain extract that inhibited crustacean muscle, focused interest on GABA as a possible inhibitory transmitter. In the first microiontophoretic tests, though GABA strongly inhibited spinal neurons, these effects were considered ‘non-specific’. Strong excitation by glutamate (and other acidic amino acids) led to the same conclusion. However, their great potency and rapid actions on cortical neurons convinced other authors that these endogenous amino acids are probably synaptic transmitters. This was partly confirmed by showing that both IPSPs and GABA greatly increased Cl? conductance, their effects having similar reversal potentials. Many anticonvulsants proving to be GABA antagonists, by the 1970s GABA became widely accepted as a mediator of IPSPs. Progress was much slower for glutamate. Being generated on distant dendrites, EPSPs could not be easily compared with glutamate-induced excitation, and the search for specific antagonists was long hampered by the lack of blockers and the variety of glutamate receptors. These difficulties were gradually overcome by the application of powerful techniques, such as single channel recording, cloning receptors, as well as new pharmacological tools.

Krnjevic, Kresimir

2010-01-01

91

Valine dehydrogenase from Streptomyces albus: gene cloning, heterologous expression and identification of active site by site-directed mutagenesis  

Microsoft Academic Search

A gene encoding valine dehydrogenase (Vdh) has been cloned from Streptomyces albus, a salinomycin producer, and expressed in Escherichia coli. The S. albus Vdh is composed of 364 amino acids that showed high homology with several other amino acid dehydrogenases as well as Vdhs from Streptomyces spp. and leucine and phenylalanine dehydrogenases (Ldh and Pdh) from Bacillus spp. A protein

Chang-Gu Hyun; Sang Suk Kim; Kwan-Hyung Park; Joo-Won Suh

2000-01-01

92

Enigmatic Isovaline: Investigating the Stability, Racemization, and Formation of a Non-biological Meteoritic Amino Acid  

NASA Technical Reports Server (NTRS)

Among the Murchison meteoritic amino acids, isovaline stands out as being both nonbiological (non-protein) and having a relatively high abundance. While approximately equal amounts of D- and L-isovaline have been reported in Murchison and other CM meteorites, the molecule's structure appears to prohibit its racemization in aqueous solutions. We recently have investigated the low-temperature solid-phase chemistry of both isovaline and valine with an eye toward each molecule's formation, stability, and possible interconversions of D and L enantiomers. Ion-irradiated isovaline- and valinecontaining ices were examined by IR spectroscopy and highly-sensitive liquid chromatography/time-of-flight mass spectral methods to assess both amino acid destruction and racemization. Samples were studied in the presence and in the absence of water-ice, and the destruction of both isovaline and valine was measured as a function of radiation dose. In addition, we have undertaken experiments to synthesize isovaline, valine, and their amino acid isomers by solid-phase radiation-chemical pathways other than the oft-invoked Strecker process. This presentation will review and summarize some of our recent findings. -- Our work has been supported by a grant to the Goddard Center for Astrobiology through the NASA Astrobiology Institute. Experiments were performed in the Cosmic Ice Laboratory (RLH, MHM, AL) and the Astrobiology Analytical Laboratory (JPD, DPG) at the NASA Goddard Space Flight Center.

Hudson, Reggie; Moore, Marla; Lewis, Ariel; Dworkin, Jason

2008-01-01

93

Nonprotein Amino Acids in the Murchison Meteorite  

PubMed Central

Twelve nonprotein amino acids appear to be present in the Murchison meteorite. The identity of eight of them has been conclusively established as N-methylglycine, ?-alanine, 2-methylalanine, ?-amino-n-butyric acid, ?-amino-n-butyric acid, ?-amino-n-butyric acid, isovaline, and pipecolic acid. Tentative evidence is presented for the presence of N-methylalanine, N-ethylglycine, ?-aminoisobutyric acid, and norvaline. These amino acids appear to be extraterrestrial in origin and may provide new evidence for the hypothesis of chemical evolution.

Kvenvolden, Keith A.; Lawless, James G.; Ponnamperuma, Cyril

1971-01-01

94

Gene inactivation in Lactococcus lactis: branched-chain amino acid biosynthesis.  

PubMed Central

The Lactococcus lactis subsp. lactis strains isolated from dairy products are auxotrophs for branched-chain amino acids (leucine, isoleucine, and valine), while most strains isolated from nondairy media are prototrophs. We have cloned and sequenced the leu genes from one auxotroph, IL1403. The sequence is 99% homologous to that of the prototroph NCDO2118, which was determined previously. Two nonsense mutations and two small deletions were found in the auxotroph sequence, which might explain the branched-chain amino acid auxotrophy. Nevertheless, the leu genes from the auxotroph appear to be transcribed and regulated similarly to those from the prototroph. Images

Godon, J J; Delorme, C; Bardowski, J; Chopin, M C; Ehrlich, S D; Renault, P

1993-01-01

95

An Amino Acid Mixture Mitigates Radiation-induced Gastrointestinal Toxicity.  

PubMed

Electrolyte and nutrient absorption occur in villous epithelial cells. Radiation often results in reduced electrolyte and nutrient absorption, which leads to gastrointestinal toxicity. Therefore, the authors studied: (1) radiation-induced changes in glucose and amino acid absorption across ileal tissues and (2) the effect of amino acid mixtures on absorptive capacity. NIH Swiss mice were irradiated (0, 1, 3, 5, or 7 Gy) using a Cs source at 0.9 Gy min. Transepithelial short circuit current (Isc), dilution potential, and isotope flux determinations were made in Ussing chamber studies and correlated to plasma endotoxin and IL-1? levels. Amino acids that increased electrolyte absorption and improved mucosal barrier functions were used to create a mitigating amino acid mixture (MAAM). The MAAM was given to mice via gastric gavage; thereafter, body weight and survival were recorded. A significant decrease in basal and glucose-stimulated sodium absorption occurred after 0, 1, 3, 5, and 7 Gy irradiation. Ussing chamber studies showed that paracellular permeability increased following irradiation and that the addition of glucose resulted in a further increase in permeability. Following irradiation, certain amino acids manifested decreased absorption, whereas others were associated with increased absorption. Lysine, aspartic acid, glycine, isoleucine, threonine, tyrosine, valine, tryptophan, and serine decreased plasma endotoxins were selected for the MAAM. Mice treated with the MAAM showed increased electrolyte absorption and decreased paracellular permeability, IL-1? levels, and plasma endotoxin levels. Mice treated with MAAM also had increased weight gain and better survival following irradiation. The MAAM has immediate potential for use in mitigating radiation-induced acute gastrointestinal syndrome. PMID:24776907

Yin, Liangjie; Vijaygopal, Pooja; Menon, Rejeesh; Vaught, Lauren A; Zhang, Mei; Zhang, Lurong; Okunieff, Paul; Vidyasagar, Sadasivan

2014-06-01

96

Amino Acid Metabolism in Uremia of Man.  

National Technical Information Service (NTIS)

The following studies on various facets of amino acid disposition and metabolism in uremic patients were carried out: (a) Assessment of the losses of amino acids during hemodialysis with the Kiil Dialyzer and the Hollow Fiber Artificial Kidney. (b) Examin...

J. H. Peters, P. F. Gulyassy

1971-01-01

97

Amino Acid Interactions in the Regulation of Nitrate Reductase Induction in Cotton Root Tips  

PubMed Central

Glycine, asparagine, and glutamine inhibited the induction by nitrate of nitrate reductase activity in root tips of cotton (Gossypium hirsutum L.). This inhibition was partially or entirely prevented when the inhibitor was applied in combination with any of several other amino acids. Studies of 14C-labeled amino acid uptake showed that, in most cases, the apparent antagonism resulted simply from competition for uptake. However, certain antagonists did not curtail uptake. The most effective of these were leucine (against all three inhibitors), and isoleucine and valine (against asparagine or glutamine, but not glycine). These results show that interactions among amino acids in the regulation of nitrate reductase induction result from at least two mechanisms, one acting on uptake of inhibitory amino acids, and the other involving true antagonism.

Radin, John W.

1977-01-01

98

Light-activated amino acid transport in Halobacterium halobium envelope vesicles  

NASA Technical Reports Server (NTRS)

Vesicles prepared from Halobacterium halobium cell envelopes accumulate amino acids in response to light-induced electrical and chemical gradients. Nineteen of 20 commonly occurring amino acids have been shown to be actively accumulated by these vesicles in response to illumination or in response to an artificially created Na+ gradient. On the basis of shared common carriers the transport systems can be divided into eight classes, each responsible for the transport of one or several amino acids: arginine, lysine, histidine; asparagine, glutamine; alanine, glycine, threonine, serine; leucine, valine, isoleucine, methionine; phenylalanine, tyrosine, tryptophan; aspartate; glutamate; proline. Available evidence suggests that these carriers are symmetrical in that amino acids can be transported equally well in both directions across the vesicle membranes. A tentative working model to account for these observations is presented.

Macdonald, R. E.; Lanyi, J. K.

1977-01-01

99

Unnatural reactive amino acid genetic code additions  

DOEpatents

This invention provides compositions and methods for producing translational components that expand the number of genetically encoded amino acids in eukaryotic cells. The components include orthogonal tRNAs, orthogonal aminoacyl-tRNA synthetases, pairs of tRNAs/synthetases and unnatural amino acids. Proteins and methods of producing proteins with unnatural amino acids in eukaryotic cells are also provided.

Deiters, Alexander; Cropp, Ashton T; Chin, Jason W; Anderson, Christopher J; Schultz, Peter G

2013-05-21

100

Unnatural reactive amino acid genetic code additions  

DOEpatents

This invention provides compositions and methods for producing translational components that expand the number of genetically encoded amino acids in eukaryotic cells. The components include orthogonal tRNAs, orthogonal aminoacyl-tRNAsyn-thetases, pairs of tRNAs/synthetases and unnatural amino acids. Proteins and methods of producing proteins with unnatural amino acids in eukaryotic cells are also provided.

Deiters, Alexander (La Jolla, CA); Cropp, T. Ashton (Bethesda, MD); Chin, Jason W. (Cambridge, GB); Anderson, J. Christopher (San Francisco, CA); Schultz, Peter G. (La Jolla, CA)

2011-08-09

101

Unnatural reactive amino acid genetic code additions  

DOEpatents

This invention provides compositions and methods for producing translational components that expand the number of genetically encoded amino acids in eukaryotic cells. The components include orthogonal tRNAs, orthogonal aminoacyl-tRNA synthetases, orthogonal pairs of tRNAs/synthetases and unnatural amino acids. Proteins and methods of producing proteins with unnatural amino acids in eukaryotic cells are also provided.

Deiters, Alexander (La Jolla, CA); Cropp, T. Ashton (San Diego, CA); Chin, Jason W. (Cambridge, GB); Anderson, J. Christopher (San Francisco, CA); Schultz, Peter G. (La Jolla, CA)

2011-02-15

102

Biochemistry and biotechnology of amino acid dehydrogenases  

Microsoft Academic Search

Over the last decade, amino acid dehydrogenases such as alanine dehydrogenase (Ala DH), leucine dehydrogenase (Leu DH), and phenylalanine dehydrogenase (Phe DH) have been applied to the enantiomer-specific synthesis and analysis of various amino acids. In perticular, amino acid dehydrogenases from thermophiles have received much attention because of their high stability. Their productivity was enhanced and the purification facilitated by

Toshihisa Ohshima; Kenji Soda

103

Amino acids as regulators of gene expression  

Microsoft Academic Search

The role of amino acids as substrates for protein synthesis is well documented. However, a function for amino acids in modulating the signal transduction pathways that regulate mRNA translation has only recently been described. Interesting, some of the signaling pathways regulated by amino acids overlap with those classically associated with the cellular response to hormones such as insulin and insulin-like

Scot R Kimball; Leonard S Jefferson

2004-01-01

104

Evolutionarily Conserved Optimization of Amino Acid Biosynthesis  

Microsoft Academic Search

The “cognate bias hypothesis” states that early in evolutionary history the biosynthetic enzymes for amino acid x gradually lost residues of x, thereby reducing the threshold for deleterious effects of x scarcity. The resulting reduction in cognate amino acid composition of the enzymes comprising a particular amino acid biosynthetic\\u000a pathway is predicted to confer a selective growth advantage on cells.

Ethan O. Perlstein; Benjamin L. de Bivort; Samuel Kunes; Stuart L. Schreiber

2007-01-01

105

An alternative model of amino acid replacement  

Microsoft Academic Search

Motivation: The observed correlations between pairs of homologous protein sequences are typically explained in terms of a Markovian dynamic of amino acid substitution. This model assumes that every location on the protein sequence has the same background distribution of amino acids, an assumption that is incompatible with the observed heterogeneity of protein amino acid profiles and with the success of

Gavin E. Crooksand; Steven E. Brenner

2005-01-01

106

40 CFR 721.1643 - Benzenesulfonic acid, amino substituted phenylazo-.  

Code of Federal Regulations, 2013 CFR

...2013-07-01 false Benzenesulfonic acid, amino substituted phenylazo-. 721... § 721.1643 Benzenesulfonic acid, amino substituted phenylazo-. ...generically as a benzenesulfonic acid, amino substituted phenylazo-...

2013-07-01

107

The retention and recovery of amino acids from pork longissimus muscle following cooking to either 60°C or 75°C.  

PubMed

Samples of pork longissimus muscle (n=16) cooked to either 60°C or 75°C in a water bath for 90 min were assessed for amino acid composition. Recovery of protein in the cooked meat plus the cooking juice was >93% and was slightly higher at 60°C (P=0.031), but retention in the meat was only 89% and 82% for the lower and higher temperatures (P<0.0001). Individual amino acids varied in recovery and retention with retention being particularly low for taurine and histidine. The balance of indispensable amino acids was less than ideal, with leucine and valine being the limiting amino acids by about 30% for both raw and cooked pork. Cooking had no detrimental effect on amino acid balance. Some examples of small effects of genotype and sex on amino acid composition of pork were shown. PMID:23954276

Wilkinson, B H P; Lee, E; Purchas, R W; Morel, P C H

2014-01-01

108

Ion Chromatography Based Urine Amino Acid Profiling Applied for Diagnosis of Gastric Cancer  

PubMed Central

Aim. Amino acid metabolism in cancer patients differs from that in healthy people. In the study, we performed urine-free amino acid profile of gastric cancer at different stages and health subjects to explore potential biomarkers for diagnosing or screening gastric cancer. Methods. Forty three urine samples were collected from inpatients and healthy adults who were divided into 4 groups. Healthy adults were in group A (n = 15), early gastric cancer inpatients in group B (n = 7), and advanced gastric cancer inpatients in group C (n = 16); in addition, two healthy adults and three advanced gastric cancer inpatients were in group D (n = 5) to test models. We performed urine amino acids profile of each group by applying ion chromatography (IC) technique and analyzed urine amino acids according to chromatogram of amino acids standard solution. The data we obtained were processed with statistical analysis. A diagnostic model was constructed to discriminate gastric cancer from healthy individuals and another diagnostic model for clinical staging by principal component analysis. Differentiation performance was validated by the area under the curve (AUC) of receiver-operating characteristic (ROC) curves. Results. The urine-free amino acid profile of gastric cancer patients changed to a certain degree compared with that of healthy adults. Compared with healthy adult group, the levels of valine, isoleucine, and leucine increased (P < 0.05), but the levels of histidine and methionine decreased (P < 0.05), and aspartate decreased significantly (P < 0.01). The urine amino acid profile was also different between early and advanced gastric cancer groups. Compared with early gastric cancer, the levels of isoleucine and valine decreased in advanced gastric cancer (P < 0.05). A diagnosis model constructed for gastric cancer with AUC value of 0.936 tested by group D showed that 4 samples could coincide with it. Another diagnosis model for clinical staging with an AUC value of 0.902 tested by 3 advanced gastric cancer inpatients of group D showed that all could coincide with the model. Conclusions. The noticeable differences of urine-free amino acid profiles between gastric cancer patients and healthy adults indicate that such amino acids as valine, isoleucine, leucine, methionine, histidine and aspartate are important metabolites in cell multiplication and gene expression during tumor growth and metastatic process. The study suggests that urine-free amino acid profiling is of potential value for screening or diagnosing gastric cancer.

Fan, Jing; Hong, Jing; Hu, Jun-Duo; Chen, Jin-Lian

2012-01-01

109

Bacterial synthesis of D-amino acids.  

PubMed

Recent work has shed light on the abundance and diversity of D-amino acids in bacterial extracellular/periplasmic molecules, bacterial cell culture, and bacteria-rich environments. Within the extracellular/periplasmic space, D-amino acids are necessary components of peptidoglycan, and disruption of their synthesis leads to cell death. As such, enzymes responsible for D-amino acid synthesis are promising targets for antibacterial compounds. Further, bacteria are shown to incorporate a diverse collection of D-amino acids into their peptidoglycan, and differences in D-amino acid incorporation may occur in response to differences in growth conditions. Certain D-amino acids can accumulate to millimolar levels in cell culture, and their synthesis is proposed to foretell movement from exponential growth phase into stationary phase. While enzymes responsible for synthesis of D-amino acids necessary for peptidoglycan (D-alanine and D-glutamate) have been characterized from a number of different bacteria, the D-amino acid synthesis enzymes characterized to date cannot account for the diversity of D-amino acids identified in bacteria or bacteria-rich environments. Free D-amino acids are synthesized by racemization or epimerization at the ?-carbon of the corresponding L-amino acid by amino acid racemase or amino acid epimerase enzymes. Additionally, D-amino acids can be synthesized by stereospecific amination of ?-ketoacids. Below, we review the roles of D-amino acids in bacterial physiology and biotechnology, and we describe the known mechanisms by which they are synthesized by bacteria. PMID:24752840

Radkov, Atanas D; Moe, Luke A

2014-06-01

110

Current topics in the biotechnological production of essential amino acids, functional amino acids, and dipeptides.  

PubMed

Amino acids play important roles in both human and animal nutrition and in the maintenance of health. Here, amino acids are classified into three groups: first, essential amino acids, which are essential to nutrition; second, functional amino acids, recently found to be important in the promotion of physiological functions; and third, dipeptides, which are used to resolve problematic features of specific free amino acids, such as their instability or insolubility. This review focusses on recent researches concerning the microbial production of essential amino acids (lysine and methionine), functional amino acids (histidine and ornithine), and a dipeptide (L-alanyl-L-glutamine). PMID:24679256

Mitsuhashi, Satoshi

2014-04-01

111

Alteration of substrate specificity of valine dehydrogenase from Streptomyces albus  

Microsoft Academic Search

The catabolism of branched chain amino acids, especially valine, appears to play an important role in furnishing building blocks for macrolide and polyether antibiotic biosyntheses. To determine the active site residues of ValDH, we previously cloned, partially characterized, and identified the active site (lysine) of Streptomyces albus ValDH. Here we report further characterization of S. albus ValDH. The molecular weight

Chang-Gu Hyun; Sang Suk Kim; In Hyung Lee; Joo-Won Suh

2000-01-01

112

Amino Acid Properties Conserved in Molecular Evolution  

PubMed Central

That amino acid properties are responsible for the way protein molecules evolve is natural and is also reasonably well supported both by the structure of the genetic code and, to a large extent, by the experimental measures of the amino acid similarity. Nevertheless, there remains a significant gap between observed similarity matrices and their reconstructions from amino acid properties. Therefore, we introduce a simple theoretical model of amino acid similarity matrices, which allows splitting the matrix into two parts – one that depends only on mutabilities of amino acids and another that depends on pairwise similarities between them. Then the new synthetic amino acid properties are derived from the pairwise similarities and used to reconstruct similarity matrices covering a wide range of information entropies. Our model allows us to explain up to 94% of the variability in the BLOSUM family of the amino acids similarity matrices in terms of amino acid properties. The new properties derived from amino acid similarity matrices correlate highly with properties known to be important for molecular evolution such as hydrophobicity, size, shape and charge of amino acids. This result closes the gap in our understanding of the influence of amino acids on evolution at the molecular level. The methods were applied to the single family of similarity matrices used often in general sequence homology searches, but it is general and can be used also for more specific matrices. The new synthetic properties can be used in analyzes of protein sequences in various biological applications.

Rudnicki, Witold R.; Mroczek, Teresa; Cudek, Pawel

2014-01-01

113

Influence of yeast strain and aging time on free amino acid changes in sparkling ciders.  

PubMed

An analytical method for the determination of free amino acids in ciders is reported. It is based on high-performance liquid chromatography with an automatic precolumn derivatization with o-phthaldehyde and 3-mercaptopropionic acid and diode array detection. The method was applied to monitor the amino acids during second fermentation of sparkling ciders. This paper reports the influence of yeast strains and aging time on the amino acid composition of sparkling ciders. The application of principal component analysis enables the ciders to be differentiated on the basis of the two factors considered (yeast strain and aging time). The first principal component, which accounts for 58% of the total variance, achieved the separation according to aging time with serine, glycine, alanine, valine, ornithine, leucine, and lysine as the most important variables. The second principal component, accounting for 28% of the explained variance, is closely related to aspartic acid and asparagine and separates the samples according to the yeast strain. PMID:16076126

Suárez Valles, Belén; Palacios García, Noemí; Rodríguez Madrera, Roberto; Picinelli Lobo, Anna

2005-08-10

114

End-product control of enzymes of branched-chain amino acid biosynthesis in Streptomyces coelicolor.  

PubMed

In streptomycetes, the branched-chain amino acids leucine, isoleucine and valine may serve as precursors for commercially important polyketides, and it is of interest to investigate whether the availability of these amino acids affects the production of the secondary metabolites derived from them. This paper reports studies on end-product control in the model organism Streptomyces coelicolor of the enzymes acetohydroxy acid synthase (AHAS) and isopropylmalate synthase (IPMS), mediating steps in the pathways to isoleucine-valine and leucine respectively. Specific activities of both enzymes were similarly affected when minimal medium was supplemented with the amino acids singly or in combination. Isoleucine alone caused a 2- to 3-fold increase, while all three amino acids caused a 5- to 8-fold decrease. Growth of an ilv auxotroph in media with limiting isoleucine gave enzyme specific activities 4- to 6-fold higher than in unsupplemented minimal medium. Spontaneous mutants were obtained by growing S. coelicolor on minimal medium containing 4-azaleucine. At lease four patterns of end-product control were found among the mutants, one of which showed high constitutive levels of both enzymes (7- and 15-fold above unsupplemented minimal medium values for AHAS and IPMS respectively). It is concluded that the variation in specific activities of the two enzymes under different physiological and genetic conditions spans a range of around 50 to 100, and that S. coelicolor has molecular mechanisms capable of producing this response. PMID:8760908

Potter, C A; Baumberg, S

1996-08-01

115

N5-(1-carboxyethyl)-ornithine, a new amino acid from the intracellular pool of Streptococcus lactis.  

PubMed Central

Intracellular concentrations of amino acids were determined in cells of Streptococcus lactis 133 during growth in complex, spent, and chemically defined media. Glutamic and aspartic acids represented the major constituents of the amino acid pool. However, organisms grown in spent medium or in defined medium supplemented with ornithine also contained unusually high levels of two additional amino acids. One of these amino acids was ornithine. The second compound exhibited properties of a neutral amino acid by coelution with valine from the amino acid analyzer. The compound did not, however, comigrate with valine or any other standard amino acid by two-dimensional thin-layer chromatography. The unknown amino acid was purified by paper and thin-layer chromatography, and its molecular structure was determined by 1H and 13C nuclear magnetic resonance spectroscopy. This new amino acid was shown to be N5-(1-carboxyethyl)-ornithine. The 14C-labeled compound was formed by cells of S. lactis 133 during growth in spent medium or defined medium containing [14C]ornithine. Formation of the derivative by resting cells required ornithine and the presence of a metabolizable sugar. N5-(1-Carboxyethyl)-ornithine was synthesized chemically from both poly-S-ornithine and (2S)-N2-carbobenzyloxy-ornithine as a 1:1 mixture of two diastereomers. The physical and chemical properties of the amino acid purified from S. lactis 133 were identical to those of one of the synthetic diastereomers. The bis-N-trifluoroacetyl-di-n-butyl esters of the natural and synthetic compounds generated identical gas chromatography-mass spectrometry spectra. A mechanism is suggested for the in vivo synthesis of N5-(1-carboxyethyl)-ornithine, and the possible functions of this new amino acid are discussed. Images

Thompson, J; Curtis, M A; Miller, S P

1986-01-01

116

Changes in amino acids and lipids during embryogenesis of European lobster, Homarus gammarus (Crustacea: Decapoda).  

PubMed

We studied the amino acid and lipid dynamics during embryogenesis of Homarus gammarus. Major essential amino acids (EAA) in the last stage of embryonic development were arginine, lysine and leucine; major nonessential amino acids (NEAA) were glutamic acid, aspartic acid, valine and glycine. The highest percent of utilization occurred in respect to EAA (27.8%), mainly due to a significant decrease (p<0.05) of methionine (38.3%) and threonine (36.0%). NEAA also decreased significantly (p<0.05, 11.4%), namely serine (38.1%), tyrosine (26.4%) and glutamic acid (25.7%). In contrast, the free amino acid content increased significantly (p<0.05) during embryonic development, especially the free nonessential amino acids (FNEAA). In the last stage, the most abundant FNEAA were glycine, proline, alanine and taurine, and the major free essential amino acids (FEAA) were arginine, lysine and leucine. Lipid content decreased significantly (p<0.05) during embryonic development. A substantial decrease in all neutral lipid classes was observed (>80% of utilization). Major fatty acids were 16:0, 18:0, 18:1n-9, 18:2n-6, 18:3n-3, 20:5n-3 and 22:6n-3. Unsaturated (UFA) and saturated fatty acids (SFA) were used up at similar rates (76.5% and 76.3%, respectively). Within UFA, monounsaturates (MUFA) were consumed more than polyunsaturates (PUFA) (82.9% and 67.5%, respectively). PMID:15649771

Rosa, R; Calado, R; Andrade, A M; Narciso, L; Nunes, M L

2005-02-01

117

Amino and fatty acids in carbonaceous meteorites  

NASA Technical Reports Server (NTRS)

Analyses of two carbonaceous meteorites have provided much of the latest evidence which seems to support Oparin's theory on the origin of life. The meteorites involved are the Murray meteorite, which fell in 1950, and the Murchison meteorite, which fell in 1969. The amino acids in the two meteorites are similar in composition. Eight of the twenty amino acids found belong to amino acids present in proteins. A number of monocarboxylic and dicarboxylic fatty acids were also found in the meteorites.

Kvenvolden, K. A.

1974-01-01

118

Electrophysiological evidence for acidic, basic, and neutral amino acid olfactory receptor sites in the catfish  

PubMed Central

Electrophysiological experiments indicate that olfactory receptors of the channel catfish, Ictalurus punctatus, contain different receptor sites for the acidic (A), basic (B), and neutral amino acids; further, at least two partially interacting neutral sites exist, one for the hydrophilic neutral amino acids containing short side chains (SCN), and the second for the hydrophobic amino acids containing long side chains (LCN). The extent of cross-adaptation was determined by comparing the electro-olfactogram (EOG) responses to 20 "test" amino acids during continuous bathing of the olfactory mucosa with water only (control) to those during each of the eight "adapting" amino acid regimes. Both the adapting and test amino acids were adjusted in concentrations to provide approximately equal response magnitudes in the unadapted state. Under all eight adapting regimes, the test EOG responses were reduced from those obtained in the unadapted state, but substantial quantitative differences resulted, depending upon the molecular structure of the adapting stimulus. Analyses of the patterns of EOG responses to the test stimuli identified and characterized the respective "transduction processes," a term used to describe membrane events initiated by a particular subset of amino acid stimuli that are intricately linked to the origin of the olfactory receptor potential. Only when the stimulus compounds interact with different transduction processes are the stimuli assumed to bind to different membrane "sites." Four relatively independent L-alpha-amino acid transduction processes (and thus at least four binding sites) identified in this report include: (a) the A process for aspartic and glutamic acids; (b) the B process for arginine and lysine; (c) the SCN process for glycine, alanine, serine, glutamine, and possibly cysteine; (d) the LCN process for methionine, ethionine, valine, norvaline, leucine, norleucine, glutamic acid-gamma-methyl ester, histidine, phenylalanine, and also possibly cysteine. The specificities of these olfactory transduction processes in the catfish are similar to those for the biochemically determined receptor sites for amino acids in other species of fishes and to amino acid transport specificities in tissues of a variety of organisms.

1984-01-01

119

Amino acid abundances and stereochemistry in hydrothermally altered sediments from the Juan de Fuca Ridge, northeastern Pacific Ocean.  

PubMed

The Juan de Fuca Ridge is a hydrothermally active, sediment covered, spreading ridge situated a few hundred kilometres off the west coast of North America in the northeastern Pacific Ocean. Sediments from seven sites drilled during the Ocean Drilling Program (ODP) Legs 139 and 168 were analyzed for total hydrolyzable amino acids (THAA), individual amino acid distributions, total organic C (TOC) and total N (TN) contents. The aim was to evaluate the effects of hydrothermal stress on the decomposition and transformation of sedimentary amino acids. Hydrolyzable amino acids account for up to 3.3% of the total organic C content and up to 12% of the total N content of the upper sediments. The total amounts of amino acids decrease significantly with depth in all drilled holes. This trend is particularly pronounced in holes with a thermal gradient of around 0.6 degrees C/m or higher. The most abundant amino acids in shallow sediments are glycine, alanine, lysine, glutamic acid, valine and histidine. The changes in amino acid distributions in low temperature holes are characterized by increased relative abundances of non-protein beta-alanine and gamma-aminobutyric acid. In high temperature holes the amino acid compositions are characterized by high abundances of glycine, alanine, serine, ornithine and histidine at depth. D/L ratios of samples with amino acid distributions similar to those found in acid hydrolysates of kerogen, indicate that racemization rates of amino acids bound by condensation reactions may be diminished. PMID:17654789

Andersson, E; Simoneit, B R; Holm, N G

2000-09-01

120

Study on Amino Acid Metabolism and Uremia.  

National Technical Information Service (NTIS)

Histidine supplementation to either low protein diet or essential amino acid diet stimulates positivity of nitrogen balance in a group of 7 uremic patients each one studied for a period of 6 weeks. Imidazoleacetic acid, imidazolepyruvic acid and formimino...

C. Giordano

1970-01-01

121

Effects of Branched-chain Amino Acids on In vitro Ruminal Fermentation of Wheat Straw  

PubMed Central

This study investigates the effects of three branched-chain amino acids (BCAA; valine, leucine, and isoleucine) on the in vitro ruminal fermentation of wheat straw using batch cultures of mixed ruminal microorganisms. BCAA were added to the buffered ruminal fluid at a concentration of 0, 2, 4, 7, or 10 mmol/L. After 72 h of anaerobic incubation, pH, volatile fatty acids (VFA), and ammonia nitrogen (NH3-N) in the ruminal fluid were determined. Dry matter (DM) and neutral detergent fiber (NDF) degradability were calculated after determining the DM and NDF in the original material and in the residue after incubation. The addition of valine, leucine, or isoleucine increased the total VFA yields (p?0.001). However, the total VFA yields did not increase with the increase of BCAA supplement level. Total branched-chain VFA yields linearly increased as the supplemental amount of BCAA increased (p<0.001). The molar proportions of acetate and propionate decreased, whereas that of butyrate increased with the addition of valine and isoleucine (p<0.05). Moreover, the proportions of propionate and butyrate decreased (p<0.01) with the addition of leucine. Meanwhile, the molar proportions of isobutyrate were increased and linearly decreased (p<0.001) by valine and leucine, respectively. The addition of leucine or isoleucine resulted in a linear (p<0.001) increase in the molar proportions of isovalerate. The degradability of NDF achieved the maximum when valine or isoleucine was added at 2 mmol/L. The results suggest that low concentrations of BCAA (2 mmol/L) allow more efficient regulation of ruminal fermentation in vitro, as indicated by higher VFA yield and NDF degradability. Therefore, the optimum initial dose of BCAA for in vitro ruminal fermentation is 2 mmol/L.

Zhang, Hui Ling; Chen, Yong; Xu, Xiao Li; Yang, Yu Xia

2013-01-01

122

Indigenous amino acids in primitive CR meteorites  

NASA Astrophysics Data System (ADS)

CR chondrites are among the most primitive meteorites. In this paper, we report the first measurements of amino acids in Antarctic CR meteorites. Three CRs, Elephant Moraine (EET) 92042, Graves Nunataks (GRA) 95229, and Grosvenor Mountains (GRO) 95577, were analyzed for their amino acid content using high-performance liquid chromatography with UV fluorescence detection (HPLC-FD) and gas chromatography-mass spectrometry (GC-MS). Our data show that EET 92042 and GRA 95229 are the most amino acid-rich chondrites ever analyzed, with total amino acid concentrations ranging from 180 ppm to 249 ppm. The most abundant amino acids present in the EET 92042 and GRA 95229 meteorites are the ?-amino acids glycine, isovaline, ?-aminoisobutyric acid (?-AIB), and alanine, with ?13C values ranging from +31.6‰ to +50.5‰. The carbon isotope results together with racemic enantiomeric ratios determined for most amino acids strongly indicate an extraterrestrial origin for these compounds. Compared to Elephant Moraine (EET) 92042 and GRA 95229, the more aqueously altered GRO 95577 is depleted in amino acids. In both CRs and CMs, the absolute amino acid abundances appear to be related to the degree of aqueous alteration in their parent bodies. In addition, the relative abundances of ?-AIB and ?-alanine in the Antarctic CRs also appear to depend on the degree of aqueous alteration.

Martins, Z.; Alexander, C. M. O. D.; Orzechowska, G. E.; Fogel, M. L.; Ehrenfreund, P.

123

Amino acids precursors in lunar finds  

NASA Technical Reports Server (NTRS)

The consistent pattern is discussed of amino acids found in lunar dust from Apollo missions. The evidence indicates that compounds yielding amino acids were implanted into the surface of the moon by the solar wind, and the kind and amounts of amino acids found on the moon are closely similar to those found in meteorites. It is concluded that there is a common cosmochemical pattern for the moom and meteorites, and this offers evidence of a common course of cosmochemical reactions for carbon.

Fox, S. W.; Harada, K.; Hare, P. E.; Hinsch, G.; Mueller, G.

1975-01-01

124

Amino acids in the Tagish Lake Meteorite  

NASA Technical Reports Server (NTRS)

High-performance liquid chromatography (HPLC) based amino acid analysis of a Tagish Lake meteorite sample recovered 3 months after the meteorite fell to Earth have revealed that the amino acid composition of Tagish Lake is strikingly different from that of the CM and CI carbonaceous chondrites. We found that the Tagish Lake meteorite contains only trace levels of amino acids (total abundance = 880 ppb), which is much lower than the total abundance of amino acids in the CI Orgueil (4100 ppb) and the CM Murchison (16 900 ppb). Because most of the same amino acids found in the Tagish Lake meteorite are also present in the Tagish Lake ice melt water, we conclude that the amino acids detected in the meteorite are terrestrial contamination. We found that the exposure of a sample of Murchison to cold water lead to a substantial reduction over a period of several weeks in the amount of amino acids that are not strongly bound to the meteorite matrix. However, strongly bound amino acids that are extracted by direct HCl hydrolysis are not affected by the leaching process. Thus even if there had been leaching of amino acids from our Tagish Lake meteorite sample during its 3 month residence in Tagish Lake ice and melt water, a Murchison type abundance of endogenous amino acids in the meteorite would have still been readily detectable. The low amino acid content of Tagish Lake indicates that this meteorite originated fiom a different type of parent body than the CM and CI chondrites. The parent body was apparently devoid of the reagents such as aldehyldes/ketones, HCN and ammonia needed for the effective abiotic synthesis of amino acids. Based on reflectance spectral measurements, Tagish Lake has been associated with P- or D-type asteroids. If the Tagish Lake meteorite was indeed derived fiom these types of parent bodies, our understanding of these primitive asteroids needs to be reevaluated with respect to their potential inventory of biologically important organic compounds.

Kminek, G.; Botta, O.; Glavin, D. P.; Bada, J. L.

2002-01-01

125

Amino Acid Free Energy Decomposition  

NASA Astrophysics Data System (ADS)

The Distance Constraint Model (DCM) describes protein thermodynamics at a coarse-grained level based on a Free Energy Decomposition (FED) that assigns energy and entropy contributions to specific molecular interactions. Application of constraint theory accounts for non-additivity in conformational entropy so that the total free energy of a system can be reconstituted from all its molecular parts. In prior work, a minimal DCM utilized a simple FED involving temperature-independent parameters indiscriminately applied to all residues. Here, we describe a residue-specific FED that depends on local conformational states. The FED of an amino acid is constructed by weighting the energy spectrums associated with local energy minimums in configuration space by absolute entropies estimated using a quasi-harmonic approximation. Interesting temperature-dependent behavior is found. Support is from NIH R01 GM073082 and a CRI postdoctoral Duke research fellowship for H. Wang.

Wang, Hui; Fairchild, Michael; Livesay, Dennis; Jacobs, Donald

2009-03-01

126

Free amino acids in atmospheric particulate matter of Venice, Italy  

NASA Astrophysics Data System (ADS)

The concentrations of free amino acids were determined in atmospheric particulate matter from the city of Venice (Italy) in order to better understand their origin. The analysis of aerosol samples was carried out via high-performance liquid chromatography coupled to a triple quadrupole tandem mass spectrometric detector (HPLC/ESI-MS/MS). The internal standard method was used and the analytical procedure was validated by evaluating the trueness, the precision, the recovery, the detection and the quantification limits. The particulate matter was collected using quartz fiber filters and extracted in methanol; after filtration the extract was directly analyzed. Forty samples were collected from April to October 2007 and the average concentrations of free amino acids in the aerosol were: alanine 35.6 pmol m -3, aspartic acid 31.1 pmol m -3, glycine 30.1 pmol m -3, glutamic acid 32.5 pmol m -3, isoleucine 2.4 pmol m -3, leucine 2.7 pmol m -3, methionine, cystine and 3-hydroxy-proline below the limit of detection, phenylalanine 2.8 pmol m -3, proline 43.3 pmol m -3, serine 8.6 pmol m -3, threonine 2.8 pmol m -3, tyrosine 1.7 pmolm -3, valine 3.8 pmol m -3, asparagine 70.2 pmol m -3, glutamine 38.0 pmol m -3, 4-hydroxy-proline 2.5 pmol m -3, methionine sulfoxide 1.1 pmol m -3, and methionine sulfone 0.1 pmol m -3. The total average concentration of these free amino acids in aerosol samples of Venice Lagoon was 334 pmol m -3. The temporal evolution and multivariate analysis indicated the photochemical origin of 4-hydroxy-proline and methionine sulfoxide and for other compounds an origin further away from the site of sampling, presumably reflecting transport from terrestrial sources.

Barbaro, Elena; Zangrando, Roberta; Moret, Ivo; Barbante, Carlo; Cescon, Paolo; Gambaro, Andrea

2011-09-01

127

Pyrolysis of amino acids - Mechanistic considerations  

NASA Technical Reports Server (NTRS)

Pyrolysis of several structurally different amino acids in a column at 500 C showed differences in the mechanisms and final products. The aliphatic protein amino acids decompose mainly by simple decarboxylation and condensation reactions, while the beta amino acids undergo deamination to unsaturated acids. Alpha amino acids with alpha alkyl substituents undergo an unusual intramolecular SN1 reaction with the formation of an intermediate alpha lactone which decomposes to yield a ketone. The alpha alkyl substituents appear to stabilize the developing negative charge formed by partial heterolytic cleavage of the alpha carbon - NH3 bond. The gamma and delta amino acids give 2-pyrrolidinone and 2-piperidone respectively, while the epsilon acids yield mixed products.

Ratcliff, M. A., Jr.; Medley, E. E.; Simmonds, P. G.

1974-01-01

128

The inhibition effect of some amino acids towards the corrosion of aluminum in 1 M HCl + 1 M H 2SO 4 solution  

Microsoft Academic Search

The inhibition effect of some amino acids towards the corrosion of aluminum in 1M HCl+1M H2SO4 solution was investigated using weight loss measurement, linear polarization and SEM techniques. The results drawn from the different techniques are comparable. The used amino acids were alanine, leucine, valine, proline, methionine, and tryptophan. The effect of inhibitor concentration and temperature against inhibitor action was

H. Ashassi-Sorkhabi; Z. Ghasemi; D. Seifzadeh

2005-01-01

129

Efficient synthesis of D-branched-chain amino acids and their labeled compounds with stable isotopes using D-amino acid dehydrogenase.  

PubMed

D-Branched-chain amino acids (D-BCAAs) such as D-leucine, D-isoleucine, and D-valine are known to be peptide antibiotic intermediates and to exhibit a variety of bioactivities. Consequently, much effort is going into achieving simple stereospecific synthesis of D-BCAAs, especially analogs labeled with stable isotopes. Up to now, however, no effective method has been reported. Here, we report the establishment of an efficient system for enantioselective synthesis of D-BCAAs and production of D-BCAAs labeled with stable isotopes. This system is based on two thermostable enzymes: D-amino acid dehydrogenase, catalyzing NADPH-dependent enantioselective amination of 2-oxo acids to produce the corresponding D-amino acids, and glucose dehydrogenase, catalyzing NADPH regeneration from NADP(+) and D-glucose. After incubation with the enzymes for 2 h at 65°C and pH 10.5, 2-oxo-4-methylvaleric acid was converted to D-leucine with an excellent yield (>99 %) and optical purity (>99 %). Using this system, we produced five different D-BCAAs labeled with stable isotopes: D-[1-(13)C,(15)N]leucine, D-[1-(13)C]leucine, D-[(15)N]leucine, D-[(15)N]isoleucine, and D-[(15)N]valine. The structure of each labeled D-amino acid was confirmed using time-of-flight mass spectrometry and nuclear magnetic resonance analysis. These analyses confirmed that the developed system was highly useful for production of D-BCAAs labeled with stable isotopes, making this the first reported enzymatic production of D-BCAAs labeled with stable isotopes. Our findings facilitate tracer studies investigating D-BCAAs and their derivatives. PMID:23661083

Akita, Hironaga; Suzuki, Hirokazu; Doi, Katsumi; Ohshima, Toshihisa

2014-02-01

130

Comparative study on free amino acid composition of wild edible mushroom species.  

PubMed

A comparative study on the amino acid composition of 11 wild edible mushroom species (Suillus bellini, Suillus luteus, Suillus granulatus, Tricholomopsis rutilans, Hygrophorus agathosmus, Amanita rubescens, Russula cyanoxantha, Boletus edulis, Tricholoma equestre, Fistulina hepatica, and Cantharellus cibarius) was developed. To define the qualitative and quantitative profiles, a derivatization procedure with dabsyl chloride was performed, followed by HPLC-UV-vis analysis. Twenty free amino acids (aspartic acid, glutamic acid, asparagine, glutamine, serine, threonine, glycine, alanine, valine, proline, arginine, isoleucine, leucine, tryptophan, phenylalanine, cysteine, ornithine, lysine, histidine, and tyrosine) were determined. B. edulis and T. equestre were revealed to be the most nutritional species, whereas F. hepatica was the poorest. The different species exhibited distinct free amino acid profiles. The quantification of the identified compounds indicated that, in a general way, alanine was the major amino acid. The results show that the analyzed mushroom species possess moderate amino acid contents, which may be relevant from a nutritional point of view because these compounds are indispensable for human health. A combination of different mushroom species in the diet would offer good amounts of amino acids and a great diversity of palatable sensations. PMID:18942845

Ribeiro, Bárbara; Andrade, Paula B; Silva, Branca M; Baptista, Paula; Seabra, Rosa M; Valentão, Patrícia

2008-11-26

131

Selective racemization of amino acid amides in the presence of amino acids  

Microsoft Academic Search

The significant differences in the racemization rates of amino acids and the corresponding amides make it possible to carry out selective racemization of amides in the presence of optically active amino acids.

I. A. Yamskov; T. V. Tikhonova; V. E. Tikhonov; V. A. Davankov

1986-01-01

132

Metabolic fate of the carboxyl-carbon of valine  

SciTech Connect

Although several C-11-carboxyl-labeled amino acids show promise for clinical use, few detailed biokinetic studies have been reported. Such information is necessary for the calculation of comprehensive radiation absorbed doses and may reveal additional clinical uses. The authors have collected data in mice at intervals between 1 and 90 m after i.v. injection of D,L-, L-, or D-valine for 22 whole organs or tissue samples and for CO/sub 2/ and urinary excretion. The enantiomers were cleanly separated by HPLC, but studies with the D,L- mixture were also done as additional assurance of purity for the separation (i.e., (D+L)/2=D,L). Elimination of C-11 from L-valine is restricted to the approx. =25% of injected activity (IA) observed as exhaled CO/sub 2/, the production of which appears completed in approx. =15 m, the exhalation in approx. =100m. The remaining 75% IA is available for incorporation directly into proteins or into coenzyme-A after deamination to 2-oxoisovalerate. The approx. =25% IA from D-valine that appears to be retained in the body probably is not converted to L-valine since virtually no CO/sub 2/ is recovered. The pancreatic content of approx. =8% of retained activity (RA) for both L- and D- valine at 90 m suggests similar localization mechanisms for the activity remaining in the body after excretion is ended. A similar correspondence of RA is seen in most other organs, the notable exceptions being the approx. =2 to 3 times higher %RA in blood and muscle for D-valine and in small intestine for L-valine. Studies such as this offer the possibility for quantitation of isolated metabolic processes, in this case production of CO/sub 2/ from 2-oxoisovalerate formed by deamination, and for separating metabolized from non-metabolized localization of C-11 when the D-amino acid can be shown to remain undegraded.

Lathrop, K.A.; Bartlett, R.D.; Faulhaber, P.F.; Harper, P.V.

1984-01-01

133

Metabolic engineering of the L-valine biosynthesis pathway in Corynebacterium glutamicum using promoter activity modulation.  

PubMed

The previously constructed strain Corynebacterium glutamicumilvNM13 with acetohydroxy acid synthase, resistant to inhibition by all three branched-chain amino acids (L-valine, L-isoleucine and L-leucine), was used as a basis to develop a new type of valine producer by genetic engineering. The main strategy was to modulate expression of the genes involved in the biosynthesis of branched-chain amino acids. The activity of the promoters P-ilvD (dihydroxyacid dehydratase) and P-ilvE (transaminase) was up-modulated and the activity of the promoters P-ilvA (threonine deaminase) and P-leuA (isopropylmalate synthase) was down-modulated by site-directed mutagenesis. A constructed weak promoter of ilvA (or leuA), which was introduced into the C. glutamicum chromosome via a gene-replacement technique reduced the biosynthetic rate of isoleucine (or leucine), which lowered the mutant growth rate and increased valine production. Overexpression of ilvD and ilvE driven by the strong mutant promoters P-ilvDM7 and P-ilvEM6 resulted in an even higher level of valine production. Thus, the strain C. glutamicum ilvNM13 DeltapanB P-ilvAM1CG P-ilvDM7 P-ilvEM6, having all mutations constructed within the chromosome, produced 136 mM valine in a 48-h cultivation. PMID:19121344

Holátko, Jirí; Elisáková, Veronika; Prouza, Marek; Sobotka, Miroslav; Nesvera, Jan; Pátek, Miroslav

2009-02-01

134

First observation of amino acid side chain dynamics in membrane proteins using high field deuterium nuclear magnetic resonance spectroscopy  

SciTech Connect

The first deuterium NMR spectra of an individual membrane protein, bacteriohodopsin in the purple membrane of Halobacterium halobium R1 has been obtained. Biosynthetic isotopic enrichment with (gamma-2H6) valine and high field Fourier transform operation permitted rapid data acquisition on intact membranes, including measurement of relaxation times. At some temperatures high quality spectra could be obtained in less than 1 s. (U-14C)Valine tracer studies indicate that less than or equal to 2% of valine added to the growth medium is broken down and incorporated into other membrane constituents. The NMR results indicate that the valine side chain is a rather rigid structure. Motion about C alpha-C beta is slow (less than 10(5) s-1) at growth temperature, while motion about C beta-C gamma is as expected fast (much greater than 10(5) s-1) at all accessible temperatures. The activation energy for methyl group rotation from spin-lattice relaxation data between -75 and 53 degrees C is approximately 2.4 kcal/mol, in good agreement with previous 1H NMR studies on solid alkanes. Preliminary data on (gamma-2H6)valine-labeled Acholeplasma laidlawii B (PG9) cell membranes are also presented. Results strongly suggest that it should now be possible to observe in great detail the motions of any type of amino acid side chain in membrane proteins, including the effects of lipid composition on protein dynamics.

Kinsey, R.A.; Kintanar, A.; Tsai, M.D.; Smith, R.L.; Janes, N.; Oldfield, E.

1981-05-10

135

Normal Raman and surface enhanced Raman spectroscopic experiments with thin layer chromatography spots of essential amino acids using different laser excitation sources  

Microsoft Academic Search

A comparative study of the feasibility and efficiency of Raman spectroscopic detection of thin layer chromatography (TLC) spots of some weak Raman scatterers (essential amino acids, namely, glycine and l-forms of alanine, serine, valine, proline, hydroxyproline, and phenylalanine) was carried out using four different visible and near-infrared (NIR) laser radiations with wavelengths of 532, 633, 785, and 1064 nm. Three

Krisztina István; Gábor Keresztury; Andrea Szép

2003-01-01

136

Amino Acid Uptake in Arbuscular Mycorrhizal Plants  

PubMed Central

We examined the extent to which arbuscular mycorrhizal (AM) fungi root improved the acquisition of simple organic nitrogen (ON) compounds by their host plants. In a greenhouse-based study, we used quantum dots (fluorescent nanoparticles) to assess uptake of each of the 20 proteinaceous amino acids by AM-colonized versus uncolonized plants. We found that AM colonization increased uptake of phenylalanine, lysine, asparagine, arginine, histidine, methionine, tryptophan, and cysteine; and reduced uptake of aspartic acid. Arbuscular mycorrhizal colonization had the greatest effect on uptake of amino acids that are relatively rare in proteins. In addition, AM fungi facilitated uptake of neutral and positively-charged amino acids more than negatively-charged amino acids. Overall, the AM fungi used in this study appeared to improve access by plants to a number of amino acids, but not necessarily those that are common or negatively-charged.

Whiteside, Matthew D.; Garcia, Maria O.; Treseder, Kathleen K.

2012-01-01

137

Evidence of selection for low cognate amino acid bias in amino acid biosynthetic enzymes  

Microsoft Academic Search

Summary If the enzymes responsible for biosynthesis of a given amino acid are repressed and the cognate amino acid pool suddenly depleted, then derepression of these enzymes and replenishment of the pool would be problematic, if the enzymes were largely composed of the cognate amino acid. In the proverbial 'Catch 22', cells would lack the necessary enzymes to make the

Rui Alves; Michael A. Savageau

2005-01-01

138

The Apollo Program and Amino Acids  

ERIC Educational Resources Information Center

Discusses the determination of hydrolyzable amino acid precursors and a group of six amino acids in the returned lunar samples of the Apollo programs. Indicates that molecular evolution is arrested at the precursor stage on the Moon because of lack of water. (CC)

Fox, Sidney W.

1973-01-01

139

Intramolecular arylation of amino acid enolates.  

PubMed

Dianionic enolates formed from N'-aryl urea derivatives of amino acids undergo intramolecular C-arylation by attack of the enolate anion on the N'-aryl ring, leading to a hydantoin derivative of a quaternary amino acid. In situ IR studies allow identification of four intermediates on the reaction pathway. PMID:24022183

Atkinson, Rachel C; Leonard, Daniel J; Maury, Julien; Castagnolo, Daniele; Volz, Nicole; Clayden, Jonathan

2013-10-28

140

Inhibitors of Aromatic Amino Acid Biosynthesis  

NSDL National Science Digital Library

This lesson will detail the biochemical mechanisms that are affected by herbicides which inhibit a plantâÂÂs ability to synthesize amino acids. The significance of amino acids and proteins will also be described. The herbicide glyphosate, will be studied at length, including the advances made by biotechnology.

141

Reexamination of Amino Acids in Lunar Soil.  

National Technical Information Service (NTIS)

Amino acids in lunar soils provide an important indicator of the level of prebiotic organic compounds on the moon. The results provide insight into the chemistry of amino acid precursors, and furthermore, given the flux of carbonaceous material to the moo...

K. L. F. Brinton J. L. Bada J. R. Arnold

1993-01-01

142

The Amino Acid Valine Is Secreted in Continuous-Flow Bacterial Biofilms  

Microsoft Academic Search

Biofilms are structured communities characterized by distinctive gene expression patterns and profound physiological changes compared to those of planktonic cultures. Here, we show that many gram-negative bacterial biofilms secrete high levels of a small-molecular-weight compound, which inhibits the growth of only Escherichia coli K-12 and a rare few other natural isolates. We demonstrate both genetically and biochemically that this molecule

Jaione Valle; Sandra Da Re; Solveig Schmid; David Skurnik; Richard D'Ari; Jean-Marc Ghigo

2008-01-01

143

Amino acid chemoreceptors of Bacillus subtilis.  

PubMed Central

Specificities of chemoreceptors for the 20 common amino acids, toward which Bacillus subtilis shows chemotaxis, were assessed by competition ("jamming") experiments using a modification of the traditional capillary assay, called the "sensitivity capillary assay." Many amino acids were sensed by at least two chemoreceptors. All the highest affinity chemoreceptors for the amino acids were distinct, except glutamate and aspartate, which may share one chemoreceptor, and tyrosine, for which the data could not be collected due to low solubility. The data suggest the hypothesis that each amino acid-chemoreceptor complex binds to a different signaler (from each amino acid-chemoreceptor complex binds to a different signaler (from which signals travel to the flagella to modify behavior appropriately), and that many of the signalers can also bind other attractant-chemoreceptor complexes as antagonists (no signals to flagella).

Ordal, G W; Villani, D P; Gibson, K J

1977-01-01

144

Unearthing the root of amino acid similarity.  

PubMed

Similarities and differences between amino acids define the rates at which they substitute for one another within protein sequences and the patterns by which these sequences form protein structures. However, there exist many ways to measure similarity, whether one considers the molecular attributes of individual amino acids, the roles that they play within proteins, or some nuanced contribution of each. One popular approach to representing these relationships is to divide the 20 amino acids of the standard genetic code into groups, thereby forming a simplified amino acid alphabet. Here, we develop a method to compare or combine different simplified alphabets, and apply it to 34 simplified alphabets from the scientific literature. We use this method to show that while different suggestions vary and agree in non-intuitive ways, they combine to reveal a consensus view of amino acid similarity that is clearly rooted in physico-chemistry. PMID:23743923

Stephenson, James D; Freeland, Stephen J

2013-10-01

145

Amino acids in the Martian meteorite Nakhla  

NASA Technical Reports Server (NTRS)

A suite of protein and nonprotein amino acids were detected with high-performance liquid chromatography in the water- and acid-soluble components of an interior fragment of the Martian meteorite Nakhla, which fell in Egypt in 1911. Aspartic and glutamic acids, glycine, alanine, beta-alanine, and gamma-amino-n-butyric acid (gamma-ABA) were the most abundant amino acids detected and were found primarily in the 6 M HCl-hydrolyzed, hot water extract. The concentrations ranged from 20 to 330 parts per billion of bulk meteorite. The amino acid distribution in Nakhla, including the D/L ratios (values range from <0.1 to 0.5), is similar to what is found in bacterially degraded organic matter. The amino acids in Nakhla appear to be derived from terrestrial organic matter that infiltrated the meteorite soon after its fall to Earth, although it is possible that some of the amino acids are endogenous to the meteorite. The rapid amino acid contamination of Martian meteorites after direct exposure to the terrestrial environment has important implications for Mars sample-return missions and the curation of the samples from the time of their delivery to Earth.

Glavin, D. P.; Bada, J. L.; Brinton, K. L.; McDonald, G. D.

1999-01-01

146

Amino acids in the Martian meteorite Nakhla  

PubMed Central

A suite of protein and nonprotein amino acids were detected with high-performance liquid chromatography in the water- and acid-soluble components of an interior fragment of the Martian meteorite Nakhla, which fell in Egypt in 1911. Aspartic and glutamic acids, glycine, alanine, ?-alanine, and ?-amino-n-butyric acid (?-ABA) were the most abundant amino acids detected and were found primarily in the 6 M HCl-hydrolyzed, hot water extract. The concentrations ranged from 20 to 330 parts per billion of bulk meteorite. The amino acid distribution in Nakhla, including the d/l ratios (values range from <0.1 to 0.5), is similar to what is found in bacterially degraded organic matter. The amino acids in Nakhla appear to be derived from terrestrial organic matter that infiltrated the meteorite soon after its fall to Earth, although it is possible that some of the amino acids are endogenous to the meteorite. The rapid amino acid contamination of Martian meteorites after direct exposure to the terrestrial environment has important implications for Mars sample-return missions and the curation of the samples from the time of their delivery to Earth.

Glavin, Daniel P.; Bada, Jeffrey L.; Brinton, Karen L. F.; McDonald, Gene D.

1999-01-01

147

Adaptational modification of serine and threonine metabolism in the liver to essential amino acid deficiency in rats  

Microsoft Academic Search

It is known that plasma serine and threonine concentrations are elevated in rats chronically fed an essential amino acid deficient\\u000a diet, but the underlying mechanisms including related gene expressions or serine and threonine concentrations in liver remained\\u000a to be elucidated. We fed rats lysine or valine deficient diet for 4 weeks and examined the mRNA expressions of serine synthesising\\u000a (3-phosphoglycerate dehydrogenase,

Kenji Nagao; Makoto Bannai; Shinobu Seki; Masato Mori; Michio Takahashi

2009-01-01

148

Study of the ternary complexes of copper with salicylidene-2-aminothiophenol and some amino acids in the solid state  

Microsoft Academic Search

The ternary complexes of copper (II) with salicylidene-2-aminothiophenol (L) and glycine, alanine, valine and histidene amino acids have been studied in solution and in solid state. The mixed ligand complexes have been isolated and characterized based on elemental analyses, IR, UV-Vis, mass spectra, magnetic moment and thermal analysis (TGA). The isolated complexes were found to have the formula [M (L)(AA)

Ahmed A. Soliman; Gehad G. Mohamed

2004-01-01

149

Gemini surfactants from natural amino acids.  

PubMed

In this review, we report the most important contributions in the structure, synthesis, physicochemical (surface adsorption, aggregation and phase behaviour) and biological properties (toxicity, antimicrobial activity and biodegradation) of Gemini natural amino acid-based surfactants, and some potential applications, with an emphasis on the use of these surfactants as non-viral delivery system agents. Gemini surfactants derived from basic (Arg, Lys), neutral (Ser, Ala, Sar), acid (Asp) and sulphur containing amino acids (Cys) as polar head groups, and Geminis with amino acids/peptides in the spacer chain are reviewed. PMID:24238395

Pérez, Lourdes; Pinazo, Aurora; Pons, Ramon; Infante, Mrosa

2014-03-01

150

Amino acid analogs for tumor imaging  

DOEpatents

The invention provides novel amino acid compounds of use in detecting and evaluating brain and body tumors. These compounds combine the advantageous properties of 1-amino-cycloalkyl-1-carboxylic acids, namely, their rapid uptake and prolonged retention in tumors with the properties of halogen substituents, including certain useful halogen isotopes including fluorine-18, iodine-123, iodine-125, iodine-131, bromine-75, bromine-76, bromine-77 and bromine-82. In one aspect, the invention features amino acid compounds that have a high specificity for target sites when administered to a subject in vivo. Preferred amino acid compounds show a target to non-target ratio of at least 5:1, are stable in vivo and substantially localized to target within 1 hour after administration. An especially preferred amino acid compound is ›.sup.18 F!-1-amino-3-fluorocyclobutane-1-carboxylic acid (FACBC). In another aspect, the invention features pharmaceutical compositions comprised of an .alpha.-amino acid moiety attached to either a four, five, or a six member carbon-chain ring. In addition, the invention features analogs of .alpha.-aminoisobutyric acid.

Goodman, Mark M. (Atlanta, GA); Shoup, Timothy (Decatur, GA)

1998-10-06

151

Amino acid analogs for tumor imaging  

DOEpatents

The invention provides novel amino acid compounds of use in detecting and evaluating brain and body tumors. These compounds combine the advantageous properties of 1-amino-cycloalkyl-1-carboxylic acids, namely, their rapid uptake and prolonged retention in tumors with the properties of halogen substituents, including certain useful halogen isotopes including fluorine-18, iodine-123, iodine-125, iodine-131, bromine-75, bromine-76, bromine-77 and bromine-82. In one aspect, the invention features amino acid compounds that have a high specificity for target sites when administered to a subject in vivo. Preferred amino acid compounds show a target to non-target ratio of at least 5:1, are stable in vivo and substantially localized to target within 1 hour after administration. An especially preferred amino acid compound is [{sup 18}F]-1-amino-3-fluorocyclobutane-1-carboxylic acid (FACBC). In another aspect, the invention features pharmaceutical compositions comprised of an {alpha}-amino acid moiety attached to either a four, five, or a six member carbon-chain ring. In addition, the invention features analogs of {alpha}-aminoisobutyric acid.

Goodman, M.M.; Shoup, T.

1998-09-15

152

Amino acid analogs for tumor imaging  

DOEpatents

The invention provides novel amino acid compounds of use in detecting and evaluating brain and body tumors. These compounds combine the advantageous properties of 1-amino-cycloalkyl-1-carboxylic acids, namely, their rapid uptake and prolonged retention in tumors with the properties of halogen substituents, including certain useful halogen isotopes including fluorine-18, iodine-123, iodine-125, iodine-131, bromine-75, bromine-76, bromine-77 and bromine-82. In one aspect, the invention features amino acid compounds that have a high specificity for target sites when administered to a subject in vivo. Preferred amino acid compounds show a target to non-target ratio of at least 5:1, are stable in vivo and substantially localized to target within 1 hour after administration. An especially preferred amino acid compound is [{sup 18}F]-1-amino-3-fluorocyclobutane-1-carboxylic acid (FACBC). In another aspect, the invention features pharmaceutical compositions comprised of an {alpha}-amino acid moiety attached to either a four, five, or a six member carbon-chain ring. In addition, the invention features analogs of {alpha}-aminoisobutyric acid.

Goodman, M.M.; Shoup, T.

1998-10-06

153

Amino acid analogs for tumor imaging  

DOEpatents

The invention provides novel amino acid compounds of use in detecting and evaluating brain and body tumors. These compounds combine the advantageous properties of 1-amino-cycloalkyl-1-carboxylic acids, namely, their rapid uptake and prolonged retention in tumors with the properties of halogen substituents, including certain useful halogen isotopes including fluorine-18, iodine-123, iodine-125, iodine-131, bromine-75, bromine-76, bromine-77 and bromine-82. In one aspect, the invention features amino acid compounds that have a high specificity for target sites when administered to a subject in vivo. Preferred amino acid compounds show a target to non-target ratio of at least 5:1, are stable in vivo and substantially localized to target within 1 hour after administration. An especially preferred amino acid compound is ›.sup.18 F!-1-amino-3-fluorocyclobutane-1-carboxylic acid (FACBC). In another aspect, the invention features pharmaceutical compositions comprised of an .alpha.-amino acid moiety attached to either a four, five, or a six member carbon-chain ring. In addition, the invention features analogs of .alpha.-aminoisobutyric acid.

Goodman, Mark M. (Atlanta, GA); Shoup, Timothy (Decatur, GA)

1998-09-15

154

Amino acid transporters: roles in amino acid sensing and signalling in animal cells.  

PubMed Central

Amino acid availability regulates cellular physiology by modulating gene expression and signal transduction pathways. However, although the signalling intermediates between nutrient availability and altered gene expression have become increasingly well documented, how eukaryotic cells sense the presence of either a nutritionally rich or deprived medium is still uncertain. From recent studies it appears that the intracellular amino acid pool size is particularly important in regulating translational effectors, thus, regulated transport of amino acids across the plasma membrane represents a means by which the cellular response to amino acids could be controlled. Furthermore, evidence from studies with transportable amino acid analogues has demonstrated that flux through amino acid transporters may act as an initiator of nutritional signalling. This evidence, coupled with the substrate selectivity and sensitivity to nutrient availability classically associated with amino acid transporters, plus the recent discovery of transporter-associated signalling proteins, demonstrates a potential role for nutrient transporters as initiators of cellular nutrient signalling. Here, we review the evidence supporting the idea that distinct amino acid "receptors" function to detect and transmit certain nutrient stimuli in higher eukaryotes. In particular, we focus on the role that amino acid transporters may play in the sensing of amino acid levels, both directly as initiators of nutrient signalling and indirectly as regulators of external amino acid access to intracellular receptor/signalling mechanisms.

Hyde, Russell; Taylor, Peter M; Hundal, Harinder S

2003-01-01

155

Application of metabolic engineering for the biotechnological production of L-valine.  

PubMed

The branched chain amino acid L-valine is an essential nutrient for higher organisms, such as animals and humans. Besides the pharmaceutical application in parenteral nutrition and as synthon for the chemical synthesis of e.g. herbicides or anti-viral drugs, L-valine is now emerging into the feed market, and significant increase of sales and world production is expected. In accordance, well-known microbial production bacteria, such as Escherichia coli and Corynebacterium glutamicum strains, have recently been metabolically engineered for efficient L-valine production under aerobic or anaerobic conditions, and the respective cultivation and production conditions have been optimized. This review summarizes the state of the art in L-valine biosynthesis and its regulation in E. coli and C. glutamicum with respect to optimal metabolic network for microbial L-valine production, genetic strain engineering and bioprocess development for L-valine production, and finally, it will shed light on emerging technologies that have the potential to accelerate strain and bioprocess engineering in the near future. PMID:24816722

Oldiges, Marco; Eikmanns, Bernhard J; Blombach, Bastian

2014-07-01

156

Branched-chain and aromatic amino acid catabolism into aroma volatiles in Cucumis melo L. fruit  

PubMed Central

The unique aroma of melons (Cucumis melo L., Cucurbitaceae) is composed of many volatile compounds biosynthetically derived from fatty acids, carotenoids, amino acids, and terpenes. Although amino acids are known precursors of aroma compounds in the plant kingdom, the initial steps in the catabolism of amino acids into aroma volatiles have received little attention. Incubation of melon fruit cubes with amino acids and ?-keto acids led to the enhanced formation of aroma compounds bearing the side chain of the exogenous amino or keto acid supplied. Moreover, L-[13C6]phenylalanine was also incorporated into aromatic volatile compounds. Amino acid transaminase activities extracted from the flesh of mature melon fruits converted L-isoleucine, L-leucine, L-valine, L-methionine, or L-phenylalanine into their respective ?-keto acids, utilizing ?-ketoglutarate as the amine acceptor. Two novel genes were isolated and characterized (CmArAT1 and CmBCAT1) encoding 45.6?kDa and 42.7?kDa proteins, respectively, that displayed aromatic and branched-chain amino acid transaminase activities, respectively, when expressed in Escherichia coli. The expression of CmBCAT1 and CmArAT1 was low in vegetative tissues, but increased in flesh and rind tissues during fruit ripening. In addition, ripe fruits of climacteric aromatic cultivars generally showed high expression of CmBCAT1 and CmArAT1 in contrast to non-climacteric non-aromatic fruits. The results presented here indicate that in melon fruit tissues, the catabolism of amino acids into aroma volatiles can initiate through a transamination mechanism, rather than decarboxylation or direct aldehyde synthesis, as has been demonstrated in other plants.

Gonda, Itay; Bar, Einat; Portnoy, Vitaly; Lev, Shery; Burger, Joseph; Schaffer, Arthur A.; Tadmor, Ya'akov; Gepstein, Shimon; Giovannoni, James J.; Katzir, Nurit; Lewinsohn, Efraim

2010-01-01

157

Oral branched-chain amino acids decrease whole-body proteolysis  

NASA Technical Reports Server (NTRS)

BACKGROUND: This study reports the effects of ingesting branched-chain amino acids (leucine, valine, and isoleucine) on protein metabolism in four men. METHODS: To calculate leg protein synthesis and breakdown, we used a new model that utilized the infusion of L-[ring-13C6]phenylalanine and the sampling of the leg arterial-venous difference and muscle biopsies. In addition, protein-bound enrichments provided for the direct calculation of muscle fractional synthetic rate. Four control subjects ingested an equivalent amount of essential amino acids (threonine, methionine, and histidine) to discern the effects of branched-chain amino acid nitrogen vs the effects of essential amino acid nitrogen. Each drink also included 50 g of carbohydrate. RESULTS: Consumption of the branched-chain and the essential amino acid solutions produced significant threefold and fourfold elevations in their respective arterial concentrations. Protein synthesis and breakdown were unaffected by branched-chain amino acids, but they increased by 43% (p < .05) and 36% (p < .03), respectively, in the group consuming the essential amino acids. However, net leg balance of phenylalanine was unchanged by either drink. Direct measurement of protein synthesis by tracer incorporation into muscle protein (fractional synthetic rate) revealed no changes within or between drinks. Whole-body phenylalanine flux was significantly suppressed by each solution but to a greater extent by the branched-chain amino acids (15% and 20%, respectively) (p < .001). CONCLUSIONS: These results suggest that branched-chain amino acid ingestion suppresses whole-body proteolysis in tissues other than skeletal muscle in normal men.

Ferrando, A. A.; Williams, B. D.; Stuart, C. A.; Lane, H. W.; Wolfe, R. R.

1995-01-01

158

Modification of fetal plasma amino acid composition by placental amino acid exchangers in vitro  

PubMed Central

Fetal growth is dependent on both the quantity and relative composition of amino acids delivered to the fetal circulation, and impaired placental amino acid supply is associated with restricted fetal growth. Amino acid exchangers can alter the composition, but not the quantity, of amino acids in the intra- and extracellular amino acid pools. In the placenta, exchangers may be important determinants of the amino acid composition in the fetal circulation. This study investigates the substrate specificity of exchange between the placenta and the feto-placental circulation. Maternal–fetal transfer of radiolabelled amino acids and creatinine were measured in the isolated perfused human placental cotyledon. Transfer of l-[14C]serine or l-[14C]leucine, and [3H]glycine, were measured in the absence of amino acids in the fetal circulation (transfer by non-exchange mechanisms) and following 10–20 ?mol boluses of unlabelled amino acids into the fetal circulation to provide substrates for exchange (transfer by exchange and non-exchange mechanisms). The ability of fetal arterial boluses of l-alanine and l-leucine to stimulate release of amino acids from the placenta was also determined using HPLC in order to demonstrate the overall pattern of amino acid release. Experiments with radiolabelled amino acids demonstrated increased maternal–fetal transfer of l-serine and l-leucine, but not glycine, following boluses of specific amino acids into the fetal circulation. l-[14C]Leucine, but not l-[14C]serine or [3H]glycine, was transferred from the maternal to the fetal circulation by non-exchange mechanisms also (P < 0.01). HPLC analysis demonstrated that fetal amino acid boluses stimulated increased transport of a range of different amino acids by 4–7 ?mol l?1 (P < 0.05). Amino acid exchange provides a mechanism to supply the fetus with amino acids that it requires for fetal growth. This study demonstrates that these transporters have the capacity to exchange micromolar amounts of specific amino acids, and suggests that they play an important role in regulating fetal plasma amino acid composition.

Cleal, Jane K; Brownbill, Paul; Godfrey, Keith M; Jackson, John M; Jackson, Alan A; Sibley, Colin P; Hanson, Mark A; Lewis, Rohan M

2007-01-01

159

Amino Acid Detection in Cometary Matter?  

NASA Astrophysics Data System (ADS)

The recent identification of amino acid structures in interstellar ice analogues [1, 2] strongly supports the assumption that amino acids are abundant in cometary matter too. Cometary matter is assumed to be built up of aggregates of interstellar dust particles. Amino acids are the molecular building blocks of proteins in living organisms. These results amplified the scientific interest in the ESA cometary mission Rosetta. The Rosetta Lander includes the Cosac experiment dedicated to the identification of chiral organic molecules in cometary matter itshape in situ \\upshape by multi column gas chromatography coupled with a reflectron time-of-flight mass spectrometer. However, the envisaged itshape in situ \\upshape amino acid analysis on the cometary surface requires special technical emphasis of the COSAC instrumentation. The context in which the amino acid identification in cometary matter is of interest will be outlined and the analytical solutions that make amino acids accessible to the COSAC instrument will be presented. A succesful identification of amino acid structures in cometary matter would help to understand the beginnings of the biomolecular evolution and the origin of the biomolecular asymmetry. [1] G.M. Muñoz Caro, U.J. Meierhenrich, W.A. Schutte, B. Barbier, A. Arcones Sergovia, H. Rosenbauer, W.H.-P. Thiemann, A. Brack, J.M. Greenberg: itshape Nature \\upshape 416 (2002), 403-406. [2] M.P. Bernstein, J.P. Dworkin, S.A. Sandford, G.W. Cooper, L.J. Allamandola: itshape Nature \\upshape 416 (2002), 401-403.

Meierhenrich, U. J.; Munoz Caro, G. M.; Thiemann, W.; Goesmann, F.; Rosenbauer, H.

2003-04-01

160

Amino Acid Degradation after Meteoritic Impact Simulation  

NASA Technical Reports Server (NTRS)

Amino acids are among the most important prebiotic molecules as it is from these precursors that the building blocks of life were formed [1]. Although organic molecules were among the components of the planetesimals making up the terrestrial planets, large amounts of primitive organic precursor molecules are believed to be exogenous in origin and to have been imported to the Earth via micrometeorites, carbonaceous meteorites and comets, especially during the early stages of the formation of the Solar System [1,2]. Our study concerns the hypothesis that prebiotic organic matter, present on Earth, was synthesized in the interstellar environment, and then imported to Earth by meteorites or micrometeorites. We are particularly concerned with the formation and fate of amino acids. We have already shown that amino acid synthesis is possible inside cometary grains under interstellar environment conditions [3]. We are now interested in the effects of space conditions and meteoritic impact on these amino acids [4-6]. Most of the extraterrestrial organic molecules known today have been identified in carbonaceous chondrite meteorites [7]. One of the components of these meteorites is a clay with a composition close to that of saponite, used in our experiments. Two American teams have studied the effects of impact on various amino acids [8,9]. [8] investigated amino acids in saturated solution in water with pressure ranges between 5.1 and 21 GPa and temperature ranges between 412 and 870 K. [9] studied amino acids in solid form associated with and without minerals (Murchison and Allende meteorite extracts) and pressure ranges between 3 and 30 GPa. In these two experiments, the amino acids survived up to 15 GPa. At higher pressure, the quantity of preserved amino acids decreases quickly. Some secondary products such as dipeptides and diketopiperazins were identified in the [8] experiment.

Bertrand, M.; Westall, F.; vanderGaast, S.; Vilas, F.; Hoerz, F.; Barnes, G.; Chabin, A.; Brack, A.

2008-01-01

161

Chemiluminometric branched chain amino acids determination with immobilized enzymes by flow-injection analysis  

Microsoft Academic Search

A tri-enzyme sensor was developed for the flow-injection determination of branched chain amino acids (L-valine, L-leucine and L-isoleucine). Leucine dehydrogenase, NADH oxidase and peroxidase were coimmobilized covalently on tresylate-hydrophilic vinyl polymer beads and packed into transparent PTFE tube (20cm×1.0 i.d.), which was used as flow cell. The calibration graph was linear for 30nM–5?M; the detection limit (signal-to-noise=3) was 10nM. The

Nobutoshi Kiba; Masaki Tachibana; Kazue Tani; Takao Miwa

1998-01-01

162

Branched-chain amino acid biosynthesis genes in Lactococcus lactis subsp. lactis.  

PubMed Central

The genes for biosynthesis of the branched-chain amino acids leucine, isoleucine, and valine in Lactococcus lactis subsp. lactis NCDO2118 were characterized by cloning, complementation in Escherichia coli and Bacillus subtilis, and nucleotide sequence analysis. Nine structural genes are clustered on a 12-kb DNA fragment in the order leuABCD ilvDBNCA. Upstream of these genes, the nucleotide sequence suggests the existence of regulation by transcriptional attenuation. Between the leuD and ilvD genes is an unexpected gene, encoding a protein which belongs to the ATP-binding cassette protein superfamily.

Godon, J J; Chopin, M C; Ehrlich, S D

1992-01-01

163

Differential effects of amino acid surface decoration on the anticancer efficacy of selenium nanoparticles.  

PubMed

The use of selenium for anticancer therapy has been heavily explored during the last decade. Amino acids (AAs) play central roles both as building blocks of proteins and intermediates in metabolism. In the present study, AAs-modified selenium nanoparticles (SeNPs@AAs) have been successfully synthesized in a simple redox system. Typical neutral (valine), acidic (aspartic acid) and basic (lysine) amino acids were used to decorate SeNPs, and the stable and homodisperse nanoparticles were characterized by zeta potential and transmission electron microscope. The result of X-ray photoelectron spectra (XPS) showed that the interaction of -NH3(+) groups of the amino acids with negative-charged SeNPs could be a driving force for dispersion of the nanoparticles. The screening of in vitro anticancer activities demonstrated that SeNPs@AAs exhibited differential growth inhibitory effects on various human cancer cell lines. Among them, SeNPs decorated by Lys displayed higher anticancer efficacy than those of valine and aspartic acid. The studies on the in vitro cellular uptake mechanisms revealed that SeNPs@AAs were internalized by cancer cells through endocytosis. Flow cytometric analysis and the determination of caspase activity indicated that treatment of the MCF-7 breast adenocarcinoma cells with SeNPs@AAs led to a dose-dependent increase in apoptosis. Moreover, it was found that SeNPs@AAs-induced ROS overproduction could be the upstream signal of caspase activation and mitochondrial dysfunction in cancer cells. Taken together, our results suggest that these amino acid biocompatible nanoparticles might have potential application as chemopreventive and chemotherapeutic agents for human cancers. PMID:24257441

Feng, Yanxian; Su, Jianyu; Zhao, Zhennan; Zheng, Wenjie; Wu, Hualian; Zhang, Yibo; Chen, Tianfeng

2014-01-28

164

Investigation of the adsorption of amino acids on Pd(1 1 1): A density functional theory study  

NASA Astrophysics Data System (ADS)

Density functional theory calculations have been used to study the adsorption of glycine, alanine, norvaline, valine, proline, cysteine, and serine on Pd(1 1 1). Most amino acids except cysteine adsorb onto the surface in a tridentate fashion through a nitrogen atom and both oxygen atoms. For cysteine, an additional bond is formed with the surface due to the strong affinity of the sulfur atom, resulting in a significantly larger adsorption energy. The adsorption patterns of amino acids we examined are supported by the shifts in vibrational frequencies associated with NHH and COO. The adsorption strength of amino acids depends on how much the molecules deform during the adsorption process. Understanding the adsorption of amino acids on Pd(1 1 1) provides fundamental information for future consideration of the interactions between their derivatives or more complicated biomolecules and metal surfaces.

James, Joanna N.; Han, Jeong Woo; Sholl, David S.

2014-05-01

165

Crystal growth, structural and thermal studies of amino acids admixtured L-arginine phosphate monohydrate single crystals  

NASA Astrophysics Data System (ADS)

To study the improved characteristics of L-arginine phosphate monohydrate (LAP) crystals, amino acids mixed LAP crystals have been grown by slow cooling method. Amino acids like glycine, L-alanine, and L-valine have been selected for doping. Optical quality bulk crystals have been harvested after a typical growth period of about twenty days. The effect of amino acids in the crystal lattice and molecular vibrational frequencies of various functional groups in the crystals have been studied using X-ray powder diffraction and Fourier Transform infrared (FTIR) analyses respectively. Thermal behavior of the amino acids mixed LAP crystals have been studied from the TG and DTG analyses. High-resolution X-ray diffraction studies have been carried out to find the crystalline nature. Optical transmission studies have been carried out by UV-vis spectrophotometer. The cut off wavelength is below 240 nm for the grown crystals.

Anandan, P.; Saravanan, T.; Parthipan, G.; Kumar, R. Mohan; Bhagavannarayana, G.; Ravi, G.; Jayavel, R.

2011-05-01

166

Keratinolytic activity of purified alkaline keratinase produced by Scopulariopsis brevicaulis (Sacc.) and its amino acids profile.  

PubMed

Sodium dodecyl sulfate-polyacrlyamide gel electrophoresis (SDS-PAGE) was used to assess the purity and molecular weight of the previously purified alkaline keratinase enzyme of Scopulariopsis brevicaulis. The enzyme was homogenous, as seen by a single band of protein, and had an apparent molecular weight of 28.5 kDa. Amino acid profile of the purified keratinase revealed that it was composed of 14 different amino acids with high proportions of glutamic acid (20.86%), alanine (14.52%), glycine (14.21%), leucine (8.59%) and serine (7.81%). The enzyme contained moderate amounts of valine (6.01%), threonine (5.58%) and phenyl alanine (5.22%). The purified enzyme of S. brevicaulis exerted a potent keratinolytic activity and was capable to hydrolyze different keratinaceous materials with highest activity on chicken feathers followed by human nails and human hair. PMID:23961113

Sharaf, Eman F; Khalil, Neveen M

2011-04-01

167

Keratinolytic activity of purified alkaline keratinase produced by Scopulariopsis brevicaulis (Sacc.) and its amino acids profile  

PubMed Central

Sodium dodecyl sulfate–polyacrlyamide gel electrophoresis (SDS–PAGE) was used to assess the purity and molecular weight of the previously purified alkaline keratinase enzyme of Scopulariopsis brevicaulis. The enzyme was homogenous, as seen by a single band of protein, and had an apparent molecular weight of 28.5 kDa. Amino acid profile of the purified keratinase revealed that it was composed of 14 different amino acids with high proportions of glutamic acid (20.86%), alanine (14.52%), glycine (14.21%), leucine (8.59%) and serine (7.81%). The enzyme contained moderate amounts of valine (6.01%), threonine (5.58%) and phenyl alanine (5.22%). The purified enzyme of S. brevicaulis exerted a potent keratinolytic activity and was capable to hydrolyze different keratinaceous materials with highest activity on chicken feathers followed by human nails and human hair.

Sharaf, Eman F.; Khalil, Neveen M.

2010-01-01

168

40 CFR 721.2584 - Dodecanoic acid, 12-amino-.  

Code of Federal Regulations, 2013 CFR

...2013-07-01 false Dodecanoic acid, 12-amino-. 721.2584 Section 721...Substances § 721.2584 Dodecanoic acid, 12-amino-. (a) Chemical substance...substance identified as dodecanoic acid, 12-amino- (PMN P-98-0823;...

2013-07-01

169

Genetics Home Reference: Aromatic l-amino acid decarboxylase deficiency  

MedlinePLUS

... OMIM Genetic disorder catalog Conditions > Aromatic l-amino acid decarboxylase deficiency On this page: Description Genetic changes ... Reviewed May 2008 What is aromatic l-amino acid decarboxylase deficiency? Aromatic l-amino acid decarboxylase (AADC) ...

170

Studies on effective atomic numbers and electron densities in amino acids and sugars in the energy range 30–1333 keV  

Microsoft Academic Search

The effective atomic numbers and electron densities of the amino acids glycine, alanine, serine, valine, threonine, leucine, isoleucine, aspartic acid, lysine, glutamic acid, histidine, phenylalanine, arginine, tyrosine, tryptophane and the sugars arabinose, ribose, glucose, galactose, mannose, fructose, rhamnose, maltose, melibiose, melezitose and raffinose at the energies 30.8, 35.0, 81.0, 145, 276.4, 302.9, 356, 383.9, 661.6, 1173 and 1332.5keV were calculated

Shivalinge Gowda; S. Krishnaveni; Ramakrishna Gowda

2005-01-01

171

Exposure of amino acids and derivatives in the Earth orbit  

Microsoft Academic Search

Amino acids and amino acid derivatives were exposed to space conditions in Earth orbit as part of the ESA BIOPAN-2 mission to test the possible delivery of extraterrestrial biological building blocks to the primitive Earth. During the Biopan-2 mission, four proteinaceous amino acids (glycine, aspartic acid, glutamic acid and tyrosine), some amino acid esters and two peptides were exposed in

Bernard Barbier; Odile Henin; François Boillot; Annie Chabin; Didier Chaput; André Brack

2002-01-01

172

Amino acid, heme, and sterol requirements of the nematode, Rhabditis maupasi.  

PubMed

Rhabditis maupasi, a nematode that occurs in the mantle cavity of Helix aspersa and related North African food snails, requires 5 amino acids (lysine, methionine, phenylalanine, tryptophane and valine) for maintenance of the stage-3 survival larvae, and 5 additional amino acids (arginine, isoleucine, leucine, threonine and, marginally, histidine) for development of these larvae into adults and for reproduction. Tyrosine is beneficial but not absolutely required for reproduction. These results were obtained with axenic R. maupasi grown in a chemically defined medium containing salts, trace metals, purines and pyrimidines, Krebs cycle intermediates, a fatty acid (butyric), vitamins, urea, and a carbohydrate (dextrose). The complete medium contained 18 amino acids; each of 18 test media was deficient in one of the amino acids. In the complete medium and in a medium lacking the "nematode nonessential" amino acids, stage-3 R. maupasi developed into adults and produced one generation of offspring. For continuous cultivation, however, the nematode also required hemin or another iron porphyrin as well as a sterol such as cholesterol. PMID:569194

Brockelman, C R; Jackson, G J

1978-10-01

173

Selective enhancement and suppression of frog gustatory responses to amino acids.  

PubMed

Properties of the receptor sites for L-amino acids in taste cells of the bullfrog (Rana catesbeiana) were examined by measuring the neural activities of the glossopharyngeal nerve under various conditions. (a) The frogs responded to 12 amino acids, but the responses to the amino acids varied with individual frogs under natural conditions. The frog tongues, however, exhibited similar responses after an alkaline treatment that removes Ca2+ from the tissue. The variation in the responses under natural conditions was apparently due to the variation in the amount of Ca2+ bound to the receptor membrane. (b) The responses to hydrophilic L-amino acids (glycine, L-alanine, L-serine, L-threonine, L-cysteine, and L-proline) were of a tonic type, but those to hydrophobic L-amino acids (L-valine, L-leucine, L-isoleucine, L-methionine, L-phenylalanine, and L-tyrptophan) were usually composed of both phasic and tonic components. (c) The properties of the tonic component were quite different from those of the phasic component: the tonic component was largely enhanced by the alkaline treatment and suppressed by the acidic treatment that increases binding of Ca2+ to the tissue. Also, the tonic component was suppressed by the presence of low concentrations of salts, or the action of pronase E, whereas the phasic component was unchanged under these conditions. These properties of the phasic component were quite similar to those of the response to hydrophobic substances such as quinine. These results suggest that the hydrophilic L-amino acids stimulate receptor protein(s) and that the hydrophobic L-amino acids stimulate both the receptor protein and a receptor site similar to that for quinine. (d) On the basis of the suppression of the responses to amino acids by salts, the mechanism of generation of the receptor potential is discussed. PMID:6972437

Yoshii, K; Kobatake, Y; Kurihara, K

1981-04-01

174

Selective enhancement and suppression of frog gustatory responses to amino acids  

PubMed Central

Properties of the receptor sites for L-amino acids in taste cells of the bullfrog (Rana catesbeiana) were examined by measuring the neural activities of the glossopharyngeal nerve under various conditions. (a) The frogs responded to 12 amino acids, but the responses to the amino acids varied with individual frogs under natural conditions. The frog tongues, however, exhibited similar responses after an alkaline treatment that removes Ca2+ from the tissue. The variation in the responses under natural conditions was apparently due to the variation in the amount of Ca2+ bound to the receptor membrane. (b) The responses to hydrophilic L-amino acids (glycine, L-alanine, L-serine, L- threonine, L-cysteine, and L-proline) were of a tonic type, but those to hydrophobic L-amino acids (L-valine, L-leucine, L-isoleucine, L- methionine, L-phenylalanine, and L-tyrptophan) were usually composed of both phasic and tonic components. (c) The properties of the tonic component were quite different from those of the phasic component: the tonic component was largely enhanced by the alkaline treatment and suppressed by the acidic treatment that increases binding of Ca2+ to the tissue. Also, the tonic component was suppressed by the presence of low concentrations of salts, or the action of pronase E, whereas the phasic component was unchanged under these conditions. These properties of the phasic component were quite similar to those of the response to hydrophobic substances such as quinine. These results suggest that the hydrophilic L-amino acids stimulate receptor protein(s) and that the hydrophobic L-amino acids stimulate both the receptor protein and a receptor site similar to that for quinine. (d) On the basis of the suppression of the responses to amino acids by salts, the mechanism of generation of the receptor potential is discussed.

1981-01-01

175

Alterations in Plasma and CSF Amino Acids, Amines and Metabolites in Hepatic Coma  

PubMed Central

The dog with an end-to-side portacaval shunt (PCS) has been extensively used as a model to investigate hepatic encephalopathy (HE) as it demonstrates a plasma amino acid pattern similar to patients with chronic liver disease. In adult mongrel dogs, the effect of PCS on plasma and CSF amino acids, octopamine (OCT), phenylethanolamine (PEA) and CSF 5-hydroxyindolacetic acid (5-HIAA), were studied. Moreover, the effect of correction of plasma amino acids by infusional techniques was investigated. Tyrosine, tryptophan and phenylalanine levels increased dramatically during the development of HE in plasma and CSF, while valine, leucine and isoleucine decreased in plasma only, but CSF levels remained stable. Plasma and CSF octopamine and phenylethanolamine and CSF 5-HIAA increased markedly as clinical features in the dogs' behavior, characteristic of hepatic encephalopathy occurred, including hypersalivation, ataxia, flapping tremor, somnolence and finally coma. Once in coma, the dogs were infused with an amino acid mixture (F080) calculated to normalize the plasma amino acid pattern. After one to eight hours, the dogs began to awake. Simultaneously, blood, and CSF aromatic amino acids returned to their control values, as did OCT, PEA and CSF 5-HIAA. If F080 infusion was stopped, biochemical alterations would appear within one week, again accompanied by clinical hepatic encephalopathy. The results indicate that the altered levels of aromatic and branched chain amino acids, octopamine and PEA in plasma and CSF correlate well with the development of HE and that correction of the plasma amino acid abnormalities improves encephalopathy simultaneously with correction of neurotransmitter derangements in CSF.

Smith, Arlan R.; Rossi-Fanelli, Filippo; Ziparo, Vincenzo; James, J. Howard; Perelle, Bernice A.; Fischer, Josef E.

1978-01-01

176

Raman and surface-enhanced Raman spectroscopy of amino acids and nucleotide bases for target bacterial vibrational mode identification  

NASA Astrophysics Data System (ADS)

Raman and surface-enhanced Raman spectroscopy (SERS) studies of bacteria have reported a wide range of vibrational mode assignments associated with biological material. We present Raman and SER spectra of the amino acids phenylalanine, tyrosine, tryptophan, glutamine, cysteine, alanine, proline, methionine, asparagine, threonine, valine, glycine, serine, leucine, isoleucine, aspartic acid and glutamic acid and the nucleic acid bases adenosine, guanosine, thymidine, and uridine to better characterize biological vibrational mode assignments for bacterial target identification. We also report spectra of the bacteria Bacillus globigii, Pantoea agglomerans, and Yersinia rhodei along with band assignments determined from the reference spectra obtained.

Guicheteau, Jason; Argue, Leanne; Hyre, Aaron; Jacobson, Michele; Christesen, Steven D.

2006-06-01

177

Lipoic Acid-Dependent Oxidative Catabolism of ?-Keto Acids in Mitochondria Provides Evidence for Branched-Chain Amino Acid Catabolism in Arabidopsis1  

PubMed Central

Lipoic acid-dependent pathways of ?-keto acid oxidation by mitochondria were investigated in pea (Pisum sativum), rice (Oryza sativa), and Arabidopsis. Proteins containing covalently bound lipoic acid were identified on isoelectric focusing/sodium dodecyl sulfate-polyacrylamide gel electrophoresis separations of mitochondrial proteins by the use of antibodies raised to this cofactor. All these proteins were identified by tandem mass spectrometry. Lipoic acid-containing acyltransferases from pyruvate dehydrogenase complex and ?-ketoglutarate dehydrogenase complex were identified from all three species. In addition, acyltransferases from the branched-chain dehydrogenase complex were identified in both Arabidopsis and rice mitochondria. The substrate-dependent reduction of NAD+ was analyzed by spectrophotometry using specific ?-keto acids. Pyruvate- and ?-ketoglutarate-dependent reactions were measured in all three species. Activity of the branched-chain dehydrogenase complex was only measurable in Arabidopsis mitochondria using substrates that represented the ?-keto acids derived by deamination of branched-chain amino acids (Val [valine], leucine, and isoleucine). The rate of branched-chain amino acid- and ?-keto acid-dependent oxygen consumption by intact Arabidopsis mitochondria was highest with Val and the Val-derived ?-keto acid, ?-ketoisovaleric acid. Sequencing of peptides derived from trypsination of Arabidopsis mitochondrial proteins revealed the presence of many of the enzymes required for the oxidation of all three branched-chain amino acids. The potential role of branched-chain amino acid catabolism as an oxidative phosphorylation energy source or as a detoxification pathway during plant stress is discussed.

Taylor, Nicolas L.; Heazlewood, Joshua L.; Day, David A.; Millar, A. Harvey

2004-01-01

178

An amino acid transporter involved in gastric acid secretion.  

PubMed

Gastric acid secretion is regulated by a variety of stimuli, in particular histamine and acetyl choline. In addition, dietary factors such as the acute intake of a protein-rich diet and the subsequent increase in serum amino acids can stimulate gastric acid secretion only through partially characterized pathways. Recently, we described in mouse stomach parietal cells the expression of the system L heteromeric amino acid transporter comprised of the LAT2-4F2hc dimer. Here we address the potential role of the system L amino acid transporter in gastric acid secretion by parietal cells in freshly isolated rat gastric glands. RT-PCR, western blotting and immunohistochemistry confirmed the expression of 4F2-LAT2 amino acid transporters in rat parietal cells. In addition, mRNA was detected for the B(0)AT1, ASCT2, and ATB(0+) amino acid transporters. Intracellular pH measurements in parietal cells showed histamine-induced and omeprazole-sensitive H+-extrusion which was enhanced by about 50% in the presence of glutamine or cysteine (1 mM), two substrates of system L amino acid transporters. BCH, a non-metabolizable substrate and a competitive inhibitor of system L amino acid transport, abolished the stimulation of acid secretion by glutamine or cysteine suggesting that this stimulation required the uptake of amino acids by system L. In the absence of histamine glutamine also stimulated H+-extrusion, whereas glutamate did not. Also, phenylalanine was effective in stimulating H+/K+-ATPase activity. Glutamine did not increase intracellular Ca2+ levels indicating that it did not act via the recently described amino acid modulated Ca2+-sensing receptor. These data suggest a novel role for heterodimeric amino acid transporters and may elucidate a pathway by which protein-rich diets stimulate gastric acid secretion. PMID:16308696

Kirchhoff, Philipp; Dave, Mital H; Remy, Christine; Kosiek, Ortrud; Busque, Stephanie M; Dufner, Matthias; Geibel, John P; Verrey, Francois; Wagner, Carsten A

2006-03-01

179

Amino Acid Metabolism in Uremia of Man.  

National Technical Information Service (NTIS)

Comparative studies on the intestinal absorption of tryptophan in normal subjects, end-stage uremics, and patients maintained by hemodialysis demonstrated that absorption of this essential amino acid is defective in the patients. Rates of clearance of the...

J. H. Peters, P. F. Gulyassy, P. Schoenfeld

1972-01-01

180

Amino Acid Biosynthesis Pathways in Diatoms  

PubMed Central

Amino acids are not only building blocks for proteins but serve as precursors for the synthesis of many metabolites with multiple functions in growth and other biological processes of a living organism. The biosynthesis of amino acids is tightly connected with central carbon, nitrogen and sulfur metabolism. Recent publication of genome sequences for two diatoms Thalassiosira pseudonana and Phaeodactylum tricornutum created an opportunity for extensive studies on the structure of these metabolic pathways. Based on sequence homology found in the analyzed diatomal genes, the biosynthesis of amino acids in diatoms seems to be similar to higher plants. However, one of the most striking differences between the pathways in plants and in diatomas is that the latter possess and utilize the urea cycle. It serves as an important anaplerotic pathway for carbon fixation into amino acids and other N-containing compounds, which are essential for diatom growth and contribute to their high productivity.

Bromke, Mariusz A.

2013-01-01

181

How to build optically active ? -amino acids  

Microsoft Academic Search

Summary Various methodologies published in the literature dealing witha-amino carboxylic acid asymmetric synthesis are presented in a digest form. In each case, only some recent or most typical works are mentioned.

M. Calmes; J. Daunis

1999-01-01

182

D-amino acids trigger biofilm disassembly.  

PubMed

Bacteria form communities known as biofilms, which disassemble over time. In our studies outlined here, we found that, before biofilm disassembly, Bacillus subtilis produced a factor that prevented biofilm formation and could break down existing biofilms. The factor was shown to be a mixture of D-leucine, D-methionine, D-tyrosine, and D-tryptophan that could act at nanomolar concentrations. D-amino acid treatment caused the release of amyloid fibers that linked cells in the biofilm together. Mutants able to form biofilms in the presence of D-amino acids contained alterations in a protein (YqxM) required for the formation and anchoring of the fibers to the cell. D-amino acids also prevented biofilm formation by Staphylococcus aureus and Pseudomonas aeruginosa. D-amino acids are produced by many bacteria and, thus, may be a widespread signal for biofilm disassembly. PMID:20431016

Kolodkin-Gal, Ilana; Romero, Diego; Cao, Shugeng; Clardy, Jon; Kolter, Roberto; Losick, Richard

2010-04-30

183

Fullerene amino acid interactions. A theoretical study  

NASA Astrophysics Data System (ADS)

In this work we explore the ability of the C 60 fullerene to interact with amino acids at the DFT-B3LYP/3-21G? level of theory. The calculations suggest that the most favorable interactions of the fullerene is with arginine, leucine, and tryptophan which is related to the backbone structure of the corresponding amino acids. We propose correlations of the dissociation energies, HOMO/LUMO band gaps and hydrophobicity constants in relation to the computed quantum chemical behavior.

Leon, Aned de; Jalbout, Abraham F.; Basiuk, Vladimr A.

2008-02-01

184

Genetically encoded fluorescent coumarin amino acids  

DOEpatents

The invention relates to orthogonal pairs of tRNAs and aminoacyl-tRNA synthetases that can incorporate the coumarin unnatural amino acid L-(7-hydroxycoumarin-4-yl) ethylglycine into proteins produced in eubacterial host cells such as E. coli. The invention provides, for example but not limited to, novel orthogonal synthetases, methods for identifying and making the novel synthetases, methods for producing proteins containing the unnatural amino acid L-(7-hydroxycoumarin-4-yl)ethylglycine and related translation systems.

Wang, Jiangyun (San Diego, CA); Xie, Jianming (San Diego, CA); Schultz, Peter G. (La Jolla, CA)

2010-10-05

185

Genetically encoded fluorescent coumarin amino acids  

DOEpatents

The invention relates to orthogonal pairs of tRNAs and aminoacyl-tRNA synthetases that can incorporate the coumarin unnatural amino acid L-(7-hydroxycoumarin-4-yl)ethylglycine into proteins produced in eubacterial host cells such as E. coli. The invention provides, for example but not limited to, novel orthogonal synthetases, methods for identifying and making the novel synthetases, methods for producing proteins containing the unnatural amino acid L-(7-hydroxycoumarin-4-yl)ethylglycine and related translation systems.

Wang, Jiangyun (San Diego, CA); Xie, Jianming (San Diego, CA); Schultz, Peter G. (La Jolla, CA)

2012-06-05

186

Amino Acid Degradation after Meteoritic Impact Simulation  

NASA Astrophysics Data System (ADS)

Our study concerns the hypothesis that prebiotic organic matter, present on Earth, was synthesized in the interstellar environment, and then imported to Earth by the meteorites or micrometeorites. We are particularly concerned with the formation and fate of amino acids. We have already shown that amino acid synthesis is possible inside cometary grains under interstellar environment conditions (Munoz Caro, et al. Nature 416, 403 (2002).). We are now interested in the effects of space conditions and meteoritic impact on these amino acids (Barbier B., et al. Planet. Space Sci. 46, 391 (1998), Barbier B., et al. , Planet. Space Sci. 50, 353 (2002) ; Boillot F., et al. Origins of Life and Evol. Biosphere 32, 359 (2002)). Most of the extraterrestrial organic molecules known today have been identified in carbonaceous chondrite meteorites. One of the components of these meteorites is a clay with a composition close to that of saponite. Thus, in order to study the effects of meteoritic impact on amino acids, three amino acids (alanine, glycine, and b-alanine) were mixed with 0,275 mg saponite clay to simulate a carbonaceous chondrite meteorite. These three amino acids were identified in the Murchison meteorite, and two of them (Gly and Ala) are used in biological systems. A pressure of 15 GPa, simulating a meteorite impact with a velocity of 1.2 km/sec was applied to this artificial meteorite at the NASA Johnson Space Center Experimental Impact Laboratory. The sample extracts show a good preservation of the amino acids : 34% of glycine, about 46% of D-alanine and about 20% of b-alanine were preserved. Another experiment has been carried out using different amino-acids and higher pressures. We are now analyzing the samples. The preparation and the analysis of samples were carried out in Orléans (France) at the Molecular Biophysics Center.

Bertrand, M.; van der Gaast, S.; Vilas, F.; Horz, F.; Barnes, G.; Barbier, B.; Chabin, A.; Braak, A.; Westall, A.

2004-11-01

187

40 CFR 721.1705 - Benzoic acid, 3-amino-, diazotized, coupled with 6-amino-4-hydroxy-2-naphthalenesulfonic acid...  

Code of Federal Regulations, 2013 CFR

...2013-07-01 false Benzoic acid, 3-amino-, diazotized, coupled with...Substances § 721.1705 Benzoic acid, 3-amino-, diazotized, coupled with...generically identified as benzoic acid, 3-amino-, diazotized, coupled...

2013-07-01

188

40 CFR 721.1705 - Benzoic acid, 3-amino-, diazotized, coupled with 6-amino-4-hydroxy-2-naphthalenesulfonic acid...  

Code of Federal Regulations, 2010 CFR

...2010-07-01 2010-07-01 false Benzoic acid, 3-amino-, diazotized, coupled...Chemical Substances § 721.1705 Benzoic acid, 3-amino-, diazotized, coupled...substance generically identified as benzoic acid, 3-amino-, diazotized,...

2010-07-01

189

40 CFR 721.1705 - Benzoic acid, 3-amino-, diazotized, coupled with 6-amino-4-hydroxy-2-naphthalenesulfonic acid...  

Code of Federal Regulations, 2010 CFR

...2009-07-01 2009-07-01 false Benzoic acid, 3-amino-, diazotized, coupled...Chemical Substances § 721.1705 Benzoic acid, 3-amino-, diazotized, coupled...substance generically identified as benzoic acid, 3-amino-, diazotized,...

2009-07-01

190

Polymers from amino acids: development of dual ester-urethane melt condensation approach and mechanistic aspects.  

PubMed

A new dual ester-urethane melt condensation methodology for biological monomers-amino acids was developed to synthesize new classes of thermoplastic polymers under eco-friendly and solvent-free polymerization approach. Naturally abundant L-amino acids were converted into dual functional ester-urethane monomers by tailor-made synthetic approach. Direct polycondensation of these amino acid monomers with commercial diols under melt condition produced high molecular weight poly(ester-urethane)s. The occurrence of the dual ester-urethane process and the structure of the new poly(ester-urethane)s were confirmed by (1)H and (13)C NMR. The new dual ester-urethane condensation approach was demonstrated for variety of amino acids: glycine, ?-alanine, L-alanine, L-leucine, L-valine, and L-phenylalanine. MALDI-TOF-MS end group analysis confirmed that the amino acid monomers were thermally stable under the melt polymerization condition. The mechanism of melt process and the kinetics of the polycondensation were studied by model reactions and it was found that the amino acid monomer was very special in the sense that their ester and urethane functionality could be selectively reacted by polymerization temperature or catalyst. The new polymers were self-organized as ?-sheet in aqueous or organic solvents and their thermal properties such as glass transition temperature and crystallinity could be readily varied using different l-amino acid monomers or diols in the feed. Thus, the current investigation opens up new platform of research activates for making thermally stable and renewable engineering thermoplastics from natural resource amino acids. PMID:22713137

Anantharaj, S; Jayakannan, M

2012-08-13

191

A biosensor for all D-amino acids using evolved D-amino acid oxidase.  

PubMed

Determination of the D-amino acid content in foods and in biological samples is a very important task. In order to achieve this goal we developed a biosensor employing the flavoenzyme D-amino acid oxidase from the yeast Rhodotorula gracilis. To produce a device in which the D-amino acid composition does not alter the results, both the wild-type and a number of mutants obtained by rational design and directed evolution approaches were used. An analysis of D-amino acid oxidase mutants activity on D-amino acid mixtures containing various ratios of neutral, acidic, and basic substrates identified the Amberzyme-immobilized T60A/Q144R/K152E and M213G mutants as the best choice: their response shows an only limited dependence on the solution composition when at least 20% of the D-amino acid is made up of D-alanine (standard error is approximately 5-9%). This is the first report, to our knowledge, demonstrating that the entire D-amino acid content can be determined by using a screen-printed electrode amperometric biosensor, with a detection limit of 0.25 mM and a mean response time of 10-15 min. The D-amino acid assay based on R. gracilis DAAO-biosensor is inexpensive, simple to perform, and rapid: the D-amino acid concentration of a variety of biological samples can be investigated using this assay. PMID:18588925

Rosini, Elena; Molla, Gianluca; Rossetti, Carlo; Pilone, Mirella S; Pollegioni, Loredano; Sacchi, Silvia

2008-07-31

192

Studying amino acid transport using liposomes.  

PubMed

The transport of amino acid across the membranes has great importance in cell metabolism. Specific experimental methodologies are required for measuring the vectorial reactions catalyzed by the membrane transporters. So far, the most widely used technique to study amino acid transport was the measure of amino acid flux in intact cell systems expressing a specific transporter. Some limitations in this procedure are caused by the presence of endogenous transporters and intracellular enzymes and by the inaccessibility of the intracellular compartment. Alternative experimental strategies which allow to reducing the interferences and improving the handling of the internal compartment would be useful to the amino acid transport knowledge.An experimental protocol, which makes use of liposomes to study the transport of amino acid mediated by the glutamine/amino acid (ASCT2) transporter, solubilized from rat kidney brush borders, is described. The procedure is based on the reconstitution of the transporter in liposomes by removal of detergent from mixed micelles of detergent, solubilized protein, and phospholipid. The transport is assayed in the formed proteoliposomes measuring the Na(+) dependent uptake of L: -[(3)H]glutamine in antiport with internal L: -glutamine. This method allows measuring the transport activity under well controlled experimental conditions and permits performing experiments which cannot be realized in intact cell systems. PMID:20013389

Indiveri, Cesare

2010-01-01

193

Amino acid requirements in humans: with a special emphasis on the metabolic availability of amino acids  

Microsoft Academic Search

Due to advances made in the development of stable isotope based carbon oxidation methods, the determination of amino acid\\u000a requirements in humans has been an active area of research for the past 2 decades. The indicator amino acid oxidation (IAAO)\\u000a method developed in our laboratory for humans has been systematically applied to determine almost all indispensable amino\\u000a acid requirements in

Rajavel Elango; Ronald O. Ball; Paul B. Pencharz

2009-01-01

194

Plasma amino acid levels and amino acid losses during continuous ambulatory peritoneal  

Microsoft Academic Search

Free amino acid losses into dialysate during a 24-h collection period and postahsorptiveplasma amino acid concentrations were measured in 14 studiesin nine clinically stable men undergoing continuous ambulatory peritoneal dialysis. Patients ingested diets containing 97 ± 18 (SD) g\\/day of protein in a metabolic research unit. Total amino acid losses were 3.4 ± 1.2 g\\/24 h and represented 3.9 ±

Joel D Kopple; Michael J Blumenkrantz; Michael R Jones; John K Moran

195

Molecular Structure of Valine  

NSDL National Science Digital Library

Valine was isolated in 1901 by the chemist Emil Fischer from casein and is acquired by hydrolyzing proteins. It is mostly found in muscles and is required for muscle metabolism, repair and growth of tissue, and maintaining nitrogen balance in the body. It can also be used in substrate recognition. However, its key role is in the muscle where it is used as an energy source. Valine reverses and treats hepatic encephalopathy, alcohol related brain damages, and degenerative neurological conditions. Research has indicated that valine aids in restoring muscle mass in people who have liver disease, any injuries, or who have had surgery. Good sources of valine are dairy, meat, grain, mushrooms, soy and peanuts.

2002-08-22

196

Evidence of Selection for Low Cognate Amino Acid Bias in Amino Acid Biosynthetic Enzymes  

PubMed Central

Summary If the enzymes responsible for biosynthesis of a given amino acid are repressed and the cognate amino acid pool suddenly depleted, then derepression of these enzymes and replenishment of the pool would be problematic, if the enzymes were largely composed of the cognate amino acid. In the proverbial ‘Catch 22’, cells would lack the necessary enzymes to make the amino acid, and they would lack the necessary amino acid to make the needed enzymes. Based on this scenario, we hypothesize that evolution would lead to the selection of amino acid biosynthetic enzymes that have a relatively low content of their cognate amino acid. We call this the ‘cognate bias hypothesis’. Here we test several implications of this hypothesis directly using data from the proteome of Escherichia coli. Several lines of evidence show that low cognate bias is evident in 15 of the 20 amino acid biosynthetic pathways. Comparison with closely related Salmonella typhimurium shows similar results. Comparison with more distantly related Bacillus subtilis shows general similarities as well as significant differences in the detailed profiles of cognate bias. Thus, selection for low cognate bias plays a significant role in shaping the amino acid composition for a large class of cellular proteins.

Alves, Rui; Savageau, Michael A.

2006-01-01

197

[Plasma amino acid profiling of "same symptom for different disease" in Uyghur medicine based on high-performance liquid chromatography].  

PubMed

Objective: To determine the plasma amino acid metabolism of "same symptom for different diseases" in different cancer patients in Uyghur medicine. Methods: Plasma amino acid concentration was tested by high-performance liquid chromatography (HPLC) in cancer patients with different symptom, and the spectral profiles were subjected to a t-test for statistical significance. Results: Compared with the healthy group, lung cancer, cervical cancer, breast cancer and gastric cancer patients with abnormal Savda had lower concentration of plasma amino acids except some amino acids. Lung cancer patients with abnormal Savda had higher concentration of plasma phenylalanine, serine, cystine, valine, isoleucine, leucine and aspartic acid than Unsavda patients (P<0.05). Cervical cancer patients with abnormal Savda had low concentration of plasma arginine, but higher concentration of plasma cystine than Unsavda patients (P<0.05). Breast cancer patients with abnormal Savda had higher concentration of plasma leucine, serine, taurine, cystine, tyrosine, valine, isoleucine and asparagine than Unsavda patients (P<0.05). Gastric cancer patients with abnormal Savda had high concentration of plasma cystine but lower concentration of plasma phenylalanine, threonine and arginine than Unsavda patients (P<0.05). Conclusion: Different tumor patients with abnormal Savda have common characteristics and significant differences. PMID:25011961

Mamtimin, Batur; Upur, Halmurat; Kong, Bin; Eli, Maynur; Turahun, Askar

2014-06-01

198

D-Amino acid oxidase: new findings.  

PubMed

The most recent research on D-amino acid oxidases and D-amino acid metabolism has revealed new, intriguing properties of the flavoenzyme and enlighted novel biotechnological uses of this catalyst. Concerning the in vivo function of the enzyme, new findings on the physiological role of D-amino acid oxidase point to a detoxifying function of the enzyme in metabolizing exogenous D-amino acids in animals. A novel role in modulating the level of D-serine in brain has also been proposed for the enzyme. At the molecular level, site-directed mutagenesis studies on the pig kidney D-amino acid oxidase and, more recently, on the enzyme from the yeast Rhodotorula gracilis indicated that the few conserved residues of the active site do not play a role in acid-base catalysis but rather are involved in substrate interactions. The three-dimensional structure of the enzyme was recently determined from two different sources: at 2.5-3.0 A resolution for DAAO from pig kidney and at 1.2-1.8 A resolution for R. gracilis. The active site can be clearly depicted: the striking absence of essential residues acting in acid-base catalysis and the mode of substrate orientation into the active site, taken together with the results of free-energy correlation studies, clearly support a hydrid transfer type of mechanism in which the orbital steering between the substrate and the isoalloxazine atoms plays a crucial role during catalysis. PMID:11130179

Pilone, M S

2000-11-01

199

Deuterium isotope effect on 13C chemical shifts of tetrabutylammonium salts of Schiff bases amino acids.  

PubMed

Deuterium isotope effects on 13C chemical shift of tetrabutylammonium salts of Schiff bases, derivatives of amino acids (glycine, L-alanine, L-phenylalanine, L-valine, L-leucine, L-isoleucine and L-methionine) and various ortho-hydroxyaldehydes in CDCl3 have been measured. The results have shown that the tetrabutylammonium salts of the Schiff bases amino acids, being derivatives of 2-hydroxynaphthaldehyde and 3,5-dibromosalicylaldehyde, exist in the NH-form, while in the derivatives of salicylaldehyde and 5-bromosalicylaldehyde a proton transfer takes place. The interactions between COO- and NH groups stabilize the proton-transferred form through a bifurcated intramolecular hydrogen bond. PMID:16741983

Rozwadowski, Z

2006-09-01

200

Capillary Electrophoresis Assay for Ubiquitin Carboxyl-Terminal Hydrolases with Chemically Synthesized Ubiquitin–Valine as Substrate  

Microsoft Academic Search

Ubiquitin is expressed in eukaryotic cells as precursors, fused via its carboxyl terminus either to other ubiquitin sequences in linear polyubiquitin arrays or to specific ribosomal proteins. In some of the polyubiquitin fusions a single amino acid (e.g., valine in humans) is attached to the carboxyl terminus. These gene products are rapidly (probably cotranslationally) cleaved by ubiquitin carboxyl-terminal hydrolase (UCH)

Kate Franklin; Robert Layfield; Michael Landon; Robert Ramage; Angus Brown; Steven Love; Thomas Muir; Kirstie Urquhart; Mary Bownes; R. John Mayer

1997-01-01

201

Molecular interactions of ?-amino acids insight into aqueous ?-cyclodextrin systems.  

PubMed

Qualitative and quantitative analysis of molecular interaction prevailing in glycine, L-alanine, L-valine and aqueous solution of ?-cyclodextrin (?-CD) have been probed by thermophysical properties. Density (?), viscosity (?), and ultrasonic speed (u) measurements have been reported at different temperatures. The extent of interaction (solute-solvent interaction) is expressed in terms of the limiting apparent molar volume ([Formula: see text]), viscosity B-coefficient and limiting apparent molar adiabatic compressibility ([Formula: see text]). The changes on the enthalpy ([Formula: see text]) and entropy ([Formula: see text]) of the encapsulation analysis give information about the driving forces governing the inclusion. The temperature dependence behaviour of partial molar quantities and group contributions to partial molar volumes has been determined for the amino acids. The trends in transfer volumes, [Formula: see text], have been interpreted in terms of solute-cosolute interactions based on a cosphere overlap model. The role of the solvent (aqueous solution of ?-CD) and the contribution of solute-solute and solute-solvent interactions to the solution complexes have also been analyzed through the derived properties. PMID:23760675

Ekka, Deepak; Roy, Mahendra Nath

2013-10-01

202

Amino acids derived from Titan tholins  

NASA Technical Reports Server (NTRS)

An organic heteropolymer (Titan tholin) was produced by continuous dc discharge through a 0.9 N2/0.1 CH4 gas mixture at 0.2 mbar pressure, roughly simulating the cloudtop atmosphere of Titan. Treatment of this tholin with 6N HCl yielded 16 amino acids by gas chromatography after derivatization of N-trifluroacetyl isopropyl esters on two different capillary columns. Identifications were confirmed by GC/MS. Glycine, aspartic acid, and alpha- and beta-alanine were produced in greatest abundance; the total yield of amino acids was approximately 10(-2), approximately equal to the yield of urea. The presence of "nonbiological" amino acids, the absence of serine, and the fact that the amino acids are racemic within experimental error together indicate that these molecules are not due to microbial or other contamination, but are derived from the tholin. In addition to the HCN, HC2CN, and (CN)2 found by Voyager, nitriles and aminonitriles should be sought in the Titanian atmosphere and, eventually, amino acids on the surface. These results suggest that episodes of liquid water in the past or future of Titan might lead to major further steps in prebiological organic chemistry on that body.

Khare, B. N.; Sagan, C.; Ogino, H.; Nagy, B.; Er, C.; Schram, K. H.; Arakawa, E. T.

1986-01-01

203

Is Diabetes Mellitus-Linked Amino Acid Signature Associated With ?-Blocker-Induced Impaired Fasting Glucose?  

PubMed

Background- The 5-amino acid (AA) signature, including isoleucine, leucine, valine, tyrosine, and phenylalanine, has been associated with incident diabetes mellitus and insulin resistance. We investigated whether this same AA signature, single-nucleotide polymorphisms in genes in their catabolic pathway, was associated with development of impaired fasting glucose (IFG) after atenolol treatment. Methods and Results- Among 234 European American participants enrolled in the Pharmacogenomic Evaluation of Antihypertensive Responses (PEAR) study and treated with atenolol for 9 weeks, we prospectively followed a nested cohort that had both metabolomics profiling and genotype data available for the development of IFG. We assessed the association between baseline circulating levels of isoleucine, leucine, valine, tyrosine, and phenylalanine, as well as single-nucleotide polymorphisms in branched-chain amino-acid transaminase 1 (BCAT1) and phenylalanine hydroxylase (PAH) with development of IFG. All baseline AA levels were strongly associated with IFG development. Each increment in standard deviation of the 5 AAs was associated with the following odds ratio and 95% confidence interval for IFG based on a fully adjusted model: isoleucine 2.29 (1.31-4.01), leucine 1.80 (1.10-2.96), valine 1.77 (1.07-2.92), tyrosine 2.13 (1.20-3.78), and phenylalanine 2.04 (1.16-3.59). The composite P value was 2×10(-5). Those with PAH (rs2245360) AA genotype had the highest incidence of IFG (P for trend=0.0003). Conclusions- Our data provide important insight into the metabolic and genetic mechanisms underlying atenolol-associated adverse metabolic effects. Clinical Trial Registration- http://www.clinicaltrials.gov; Unique Identifier: NCT00246519. PMID:24627569

Cooper-Dehoff, Rhonda M; Hou, Wei; Weng, Liming; Baillie, Rebecca A; Beitelshees, Amber L; Gong, Yan; Shahin, Mohamed H A; Turner, Stephen T; Chapman, Arlene; Gums, John G; Boyle, Stephen H; Zhu, Hongjie; Wikoff, William R; Boerwinkle, Eric; Fiehn, Oliver; Frye, Reginald F; Kaddurah-Daouk, Rima; Johnson, Julie A

2014-04-01

204

Forward targeting of Toxoplasma gondii proproteins to the micronemes involves conserved aliphatic amino acids.  

PubMed

Like other apicomplexan parasites, Toxoplasma gondii actively invades host cells using a combination of secretory proteins and an acto-myosin motor system. Micronemes are the first set of proteins secreted during invasion that play an essential role in host cell entry. Many microneme proteins (MICs) function in protein complexes, and each complex contains at least one protein that displays a cleavable propeptide. Although MIC propeptides have been implicated in forward targeting to micronemes, the specific amino acids involved have not been identified. It was also not known if the propeptide has a general function in MICs trafficking in T. gondii and other apicomplexans. Here we show that propeptide domains are extensively interchangeable between T. gondii MICs and also with that of Eimeria tenella MIC5 (EtMIC5), suggesting a common mechanism of function. We also performed N-terminal deletion and mutational analysis of M2AP and MIC5 propeptides to show that a valine at position +3 (relative to signal peptidase cleavage) of proM2AP and a leucine at position +1 of proMIC5 are crucial for targeting to micronemes. Valine and leucine are closely related amino acids with similar side chains, implying a similar mode of function, a notion that was confirmed by correct trafficking of TgM2AP-V/L and TgMIC5-L/V substitution mutants. Propeptides of AMA1, MIC3 and EtMIC5 have valine or leucine at or near the N-termini and mutagenesis of these conserved residues validated their role in microneme trafficking. Collectively, our findings suggest that discrete, aliphatic residues at the extreme N-termini of proMICs facilitate trafficking to the micronemes. PMID:21438967

Gaji, Rajshekhar Y; Flammer, Halley P; Carruthers, Vern B

2011-07-01

205

Forward targeting of Toxoplasma gondii proproteins to the micronemes involves conserved aliphatic amino acids  

PubMed Central

Like other apicomplexan parasites, Toxoplasma gondii actively invades host cells using a combination of secretory proteins and an acto-myosin motor system. Micronemes are the first set of proteins secreted during invasion that play an essential role in host cell entry. Many microneme proteins (MICs) function in protein complexes, and each complex contains at least one protein that displays a cleavable propeptide. Although MIC propeptides have been implicated in forward targeting to micronemes, the specific amino acids involved have not been identified. It was also not known if the propeptide has a general function in MICs trafficking in T. gondii and other apicomplexans. Here we show that propeptide domains are extensively interchangeable between T. gondii MICs and also with that of Eimeria tenella MIC5 (EtMIC5), suggesting a common mechanism of function. We also performed N-terminal deletion and mutational analysis of M2AP and MIC5 propeptides to show that a valine at position +3 (relative to signal peptidase cleavage) of proM2AP and a leucine at position +1 of proMIC5 are crucial for targeting to micronemes. Valine and leucine are closely related amino acids with similar side chains, implying a similar mode of function, a notion that was confirmed by correct trafficking of TgM2AP-V/L and TgMIC5-L/V substitution mutants. Propeptides of AMA1, MIC3, and EtMIC5 have valine or leucine at or near the N-termini and mutagenesis of these conserved residues validated their role in microneme trafficking. Collectively, our findings suggest that discrete, aliphatic residues at the extreme N-termini of proMICs facilitate trafficking to the micronemes.

Gaji, Rajshekhar Y.; Flammer, Halley P.; Carruthers, Vern B.

2011-01-01

206

Homocysteine toxicity in Escherichia coli is caused by a perturbation of branched-chain amino acid biosynthesis.  

PubMed

In Escherichia coli the sulfur-containing amino acid homocysteine (Hcy) is the last intermediate on the methionine biosynthetic pathway. Supplementation of a glucose-based minimal medium with Hcy at concentrations greater than 0.2 mM causes the growth of E. coli Frag1 to be inhibited. Supplementation of Hcy-treated cultures with combinations of branched-chain amino acids containing isoleucine or with isoleucine alone reversed the inhibitory effects of Hcy on growth. The last intermediate of the isoleucine biosynthetic pathway, alpha-keto-beta-methylvalerate, could also alleviate the growth inhibition caused by Hcy. Analysis of amino acid pools in Hcy-treated cells revealed that alanine, valine, and glutamate levels are depleted. Isoleucine could reverse the effects of Hcy on the cytoplasmic pools of valine and alanine. Supplementation of the culture medium with alanine gave partial relief from the inhibitory effects of Hcy. Enzyme assays revealed that the first step of the isoleucine biosynthetic pathway, catalyzed by threonine deaminase, was sensitive to inhibition by Hcy. The gene encoding threonine deaminase, ilvA, was found to be transcribed at higher levels in the presence of Hcy. Overexpression of the ilvA gene from a plasmid could overcome Hcy-mediated growth inhibition. Together, these data indicate that in E. coli Hcy toxicity is caused by a perturbation of branched-chain amino acid biosynthesis that is caused, at least in part, by the inhibition of threonine deaminase. PMID:15968045

Tuite, Nina L; Fraser, Katy R; O'byrne, Conor P

2005-07-01

207

Detection of non-protein amino acids in the presence of protein amino acids. II.  

NASA Technical Reports Server (NTRS)

Studies conducted with the JEOL 5AH amino acid analyzer are described. This instrument makes possible the programming of the chromatographic process. Data are presented showing the separations of seventeen non-protein amino acids in the presence of eighteen protein amino acids. It is pointed out that distinct separations could be obtained in the case of a number of chemically similar compounds, such as ornithine and lysine, N-amidino alanine and arginine, and iminodiacetic acid and S-carboxymethyl cysteine and aspartic acid.

Shapshak, P.; Okaji, M.

1972-01-01

208

Branched Chain Amino Acid Metabolism in the Biosynthesis of Lycopersicon pennellii Glucose Esters 1  

PubMed Central

Lycopersicon pennellii Corr. (D'Arcy) an insect-resistant, wild tomato possesses high densities of glandular trichomes which exude a mixture of 2,3,4-tri-O-acylated glucose esters that function as a physical impediment and feeding deterrent to small arthropod pests. The acyl moieties are branched C4 and C5 acids, and branched and straight chain C10, C11, and C12 acids. The structure of the branched acyl constituents suggests that the branched chain amino acid biosynthetic pathway participates in their biosynthesis. [14C]Valine and deuterated branched chain amino acids (and their oxo-acid derivatives) were incorporated into branched C4 and C5 acid groups of glucose esters by a process of transamination, oxidative decarboxylation and subsequent acylation. C4 and C5 branched acids were elongated by two carbon units to produce the branched C10-C12 groups. Norvaline, norleucine, allylglycine, and methionine also were processed into acyl moieties and secreted from the trichomes as glucose esters. Changes in the acyl composition of the glucose esters following sulfonylurea herbicide administration support the participation of acetohydroxyacid synthetase and the other enzymes of branched amino acid biosynthesis in the production of glucose esters.

Walters, Donald S.; Steffens, John C.

1990-01-01

209

Amino Acids Profiles in Biological Media  

SciTech Connect

An accurate analytical method was developed to determine amino acids in some biological specimens by GC/MS technique. Stable isotopes provide useful tools for a variety of studies, offering ideal internal standards in quantitative information. Isotopic dilution gas chromatography--mass spectrometry (ID-GC/MS) is the techniques used for quantitative analysis of compounds labeled with stable isotopes. A Trace DSQ Thermo Finnigan quadrupole mass spectrometer coupled with a Trace GC was used. Amino acids were separated on a Rtx-5 MS capillary column, 30 mx0.25 mm, 0.25 {mu}m film thickness, using a temperature program from 50 deg. C, 1 min, 6 deg. C/min at 100 deg. C, 4 deg. C/min at 200 deg. C, 20 deg. C/min at 300 deg. C, (3 min). The transfer line temperature was 250 deg. C, the injector temperature 200 deg. C and ion source temperature 250 deg. C; splitter: 10:1. Electron energy was 70 eV and emission current, 100 {mu}A. The amino acids were purified on a Dowex 50W-W8 exchange resin and were derivatized in a procedure following two steps to obtain trifluoroacetyl butyl esters. The identification of amino acids was obtained by using NIST library but also by using amino acid standards.

Iordache, A. [National R and D Institute of Cryogenics and Isotopic Technologies-ICSI Rm. Valcea, 4 Uzinei St., Rm. Valcea, 240050 (Romania); Horj, E.; Morar, S.; Cozar, O.; Culea, M. ['Babes-Bolyai' University, 1 M. Kogalniceanu St., Cluj-Napoca, 400084 (Romania); Ani, A. R. [University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca-USAMV, 3-5 Manastur St., 400372 Cluj-Napoca (Romania); Mesaros, C. [University of Medicine and Pharmacy, 38 Gh. Marinescu St., 540000, Targu Mures (Romania)

2010-08-04

210

Amino Acids Profiles in Biological Media  

NASA Astrophysics Data System (ADS)

An accurate analytical method was developed to determine amino acids in some biological specimens by GC/MS technique. Stable isotopes provide useful tools for a variety of studies, offering ideal internal standards in quantitative information. Isotopic dilution gas chromatography-mass spectrometry (ID-GC/MS) is the techniques used for quantitative analysis of compounds labeled with stable isotopes. A Trace DSQ Thermo Finnigan quadrupole mass spectrometer coupled with a Trace GC was used. Amino acids were separated on a Rtx-5 MS capillary column, 30 m×0.25 mm, 0.25 ?m film thickness, using a temperature program from 50 °C, 1 min, 6 °C/min at 100 °C, 4 °C/min at 200 °C, 20 °C/min at 300 °C, (3 min). The transfer line temperature was 250 °C, the injector temperature 200 °C and ion source temperature 250 °C splitter: 10:1. Electron energy was 70 eV and emission current, 100 ?A. The amino acids were purified on a Dowex 50W-W8 exchange resin and were derivatized in a procedure following two steps to obtain trifluoroacetyl butyl esters. The identification of amino acids was obtained by using NIST library but also by using amino acid standards.

Iordache, A.; Horj, E.; Ani, A. R.; Mesaros, C.; Morar, S.; Cozar, O.; Culea, M.

2010-08-01

211

Perceived Cost of Auxotrophic Amino Acids in Two Bacterial Species  

Microsoft Academic Search

Amino acid biosynthetic pathways are highly conserved throughout all domains of life. Biosynthesis of amino acid requires the diversion of resources from energy production to amino acid production. The consequent energy-cost of producing an individual amino acid is can be estimated by addingthe amount of ATP expended in production itself to the amount of potential energy lost. Some organisms lack

Esley M. Heizer Jr; D. W. Raiford; M. L. Raymer; D. E. Krane

2009-01-01

212

Immunonutrition: role of sulfur amino acids, related amino acids, and polyamines  

Microsoft Academic Search

Pro-inflammatory cytokines mediate widespread changes in protein metabolism. Amino acids released from peripheral tissues fulfill a number of functions. They act as substrate for acute phase protein and immunoglobulin synthesis and, together with polyamines, in the replication of immune cells. Demands for specific amino acids may outstrip the supply from endogenous sources. A number of strands of evidence suggest that

Robert F. Grimble; George K. Grimble

1998-01-01

213

Characterization of antimicrobial, cytotoxic, and antiendotoxin properties of short peptides with different hydrophobic amino acids at "a" and "d" positions of a heptad repeat sequence.  

PubMed

To understand the influence of different hydrophobic amino acids at "a" and "d" positions of a heptad repeat sequence on antimicrobial, cytotoxic, and antiendotoxin properties, four 15-residue peptides with leucine (LRP), phenylalanine (FRP), valine (VRP), and alanine (ARP) residues at these positions were designed, synthesized, and characterized. Although valine is similarly hydrophobic to leucine and phenylalanine, VRP showed significantly lesser cytotoxicity than LRP and FRP; further, the replacement of leucines with valines at "a" and "d" positions of melittin-heptads drastically reduced its cytotoxicity. However, all four peptides exhibited significant antimicrobial activities that correlate well with their interactions with mammalian and bacterial cell membranes and the corresponding lipid vesicles. LRP most efficiently neutralized the LPS-induced pro-inflammatory mediators like NO, TNF-?, and IL-6 in macrophages followed by FRP, VRP, and ARP. The results could be useful for designing short antimicrobial and antiendotoxin peptides with understanding the basis of their activity. PMID:23324083

Azmi, Sarfuddin; Srivastava, Saurabh; Mishra, Nripendra N; Tripathi, Jitendra K; Shukla, Praveen K; Ghosh, Jimut Kanti

2013-02-14

214

Economic aspects of amino acids production.  

PubMed

Amino acids represent basic elements of proteins, which as a main source of nutrition themselves serve as a major reserve for maintaining essential functions of humans as well as animals. Taking the recent state of scientific knowledge into account, the industrial sector of amino acids is a priori "suitable" to a specific kind of an ecologically sound way of production, which is based on biotechnology. The following article may point out characteristics of this particular industrial sector and illustrates the applicability of the latest economic methods, founded on development of the discipline of bionics in order to describe economic aspects of amino acids markets. The several biochemical and technological fields of application of amino acids lead to specific market structures in high developed and permanently evolving systems. The Harvard tradition of industrial economics explains how market structures mould the behaviour of the participants and influences market results beyond that. A global increase in intensity of competition confirms the notion that the supply-side is characterised by asymmetric information in contrast to Kantzenbachs concept of "narrow oligopoly" with symmetrical shared knowledge about market information. Departing from this point, certain strategies of companies in this market form shall be derived. The importance of Research and Development increases rapidly and leads to innovative manufacturing methods which replace more polluting manufacturing processes like acid hydrolysis. In addition to these modifications within the production processes the article deals furthermore with the pricing based on product life cycle concept and introduces specific applications of tools like activity based costing and target costing to the field of amino acid production. The authors come to the conclusion that based on a good transferability of latest findings in bionics and ecological compatibility competitors in amino acids manufacturing are well advised to exercise concepts of the management of complex systems in order to choose the right strategy towards gaining market leadership. PMID:12523391

Mueller, Udo; Huebner, Susanna

2003-01-01

215

Early parenteral feeding of amino acids.  

PubMed Central

Serial 24 hour balance studies of nitrogen and energy were carried out over 10 days in two groups of ventilator dependent preterm infants, of comparable weight and gestational age. In one group (n = 10) a parenteral amino acid source (Vamin 9) was started within 24 hours of birth, and in the other group (n = 11) it was not started until 72 hours. The feeding protocol was otherwise identical. The nitrogen intake (286 compared with 21 mg/kg/day), energy intake (188 compared with 151 kJ), and nitrogen retention (120 compared with -133 mg/kg/day), were all significantly higher during the first three days of life in the group in which the amino acid solution was started early. There were no differences by 7-10 days. The early introduction of amino acids improves the early nutritional state of sick preterm infants.

Saini, J; MacMahon, P; Morgan, J B; Kovar, I Z

1989-01-01

216

Cometary Amino Acids from the STARDUST Mission  

NASA Technical Reports Server (NTRS)

NASA's Stardust spacecraft returned samples from comet 81 P/WiId 2 to Earth in January 2006. Examinations of the organic compounds in cometary samples can reveal information about the prebiotic organic inventory present on the early Earth and within the early Solar System, which may have contributed to the origin of life. Preliminary studies of Stardust material revealed the presence of a suite of organic compounds including several amines and amino acids, but the origin of these compounds (cometary vs. terrestrial contamination) could not be identified. We have recently measured the carbon isotopic ratios of these amino acids to determine their origin, leading to the first detection of a cometary amino acid.

Cook, Jamie Elsila

2009-01-01

217

Glutamate: a truly functional amino acid.  

PubMed

Glutamate is one of the most abundant of the amino acids. In addition to its role in protein structure, it plays critical roles in nutrition, metabolism and signaling. Post-translational carboxylation of glutamyl residues increases their affinity for calcium and plays a major role in hemostasis. Glutamate is of fundamental importance to amino acid metabolism, yet the great bulk of dietary glutamate is catabolyzed within the intestine. It is necessary for the synthesis of key molecules, such as glutathione and the polyglutamated folate cofactors. It plays a major role in signaling. Within the central nervous system, glutamate is the major excitatory neurotransmitter and its product, GABA, the major inhibitory neurotransmitter. Glutamate interaction with specific taste cells in the tongue is a major component of umami taste. The finding of glutamate receptors throughout the gastrointestinal tract has opened up a new vista in glutamate function. Glutamate is truly a functional amino acid. PMID:22526238

Brosnan, John T; Brosnan, Margaret E

2013-09-01

218

Apical Transporters for Neutral Amino Acids: Physiology and Pathophysiology  

NSDL National Science Digital Library

Absorption of amino acids in kidney and intestine involves a variety of transporters for different groups of amino acids. This is illustrated by inherited disorders of amino acid absorption, such as Hartnup disorder, cystinuria, iminoglycinuria, dicarboxylic aminoaciduria, and lysinuric protein intolerance, affecting separate groups of amino acids. Recent advances in the molecular identification of apical neutral amino acid transporters has shed a light on the molecular basis of Hartnup disorder and iminoglycinuria.

Stefan Broer (Australian National University)

2008-04-01

219

Nutrient composition and amino acid pattern of cowpea (Vigna unguiculata (L.) Walp, Fabaceae) grown in the Gizan area of Saudi Arabia.  

PubMed

The proximate composition, grain protein, minerals, amino acid and sugar profiles of Vigna unguiculata (L.) Walp were analyzed. The crude protein was 23%, fat 3.40% and ash 3.60%. Amino acid analysis indicated the presence of at least 17 amino acids including most of the essential ones. The essential amino acids valine, leucine, phenylalanine and lysine were slightly higher, but sulphur-containing amino acids were lower than recommended in the WHO/FAO requirement pattern. Qualitative phytochemical screening of seeds showed fructose, alpha-glucose, beta-glucose, glycerol, manitol, inositol and some oligosaccharides, e.g. raffinose, stachyose, and verbascose. The grain contained almost similar amount of phosphorus as compared with that of Lebanese and Pakistani cultivars. Calcium was found to be lower as compared to some Indian, Pakistani and Lebanese cultivars. In general the results indicated that the legume is nutritive as staple food, feed and/or fodder. PMID:9713582

Hussain, M A; Basahy, A Y

1998-03-01

220

CSF gradients for amino acid neurotransmitters.  

PubMed Central

Amino acid concentrations were measured in CSF samples obtained by lumbar puncture in 51 patients, cervical puncture in 16 patients, spinal drains in nine patients, ventricular taps in five patients and from below a spinal block in six patients. There was evidence of a rostrocaudal gradient for GABA and taurine and a reverse gradient for alanine and asparagine. Lumbar CSF glycine concentrations rose with increasing age whilst GABA concentrations fell. Women had significantly lower concentrations of asparagine and glutamine and elevated taurine compared to men. The influence of biological factors and gradients must be taken into account before the interpretation of changes in CSF amino acid concentrations.

Crawford, P M; Lloyd, K G; Chadwick, D W

1988-01-01

221

The Genetics of Heteromeric Amino Acid Transporters  

NSDL National Science Digital Library

Heteromeric amino acid transporters (HATs) are composed of a heavy (SLC3 family) and a light (SLC7 family) subunit. Mutations in system b0,+ (rBAT-b0,+AT) and in system y+L (4F2hc-y+LAT1) cause the primary inherited aminoacidurias (PIAs) cystinuria and lysinuric protein intolerance, respectively. Recent developments [including the identification of the first Hartnup disorder gene (B0AT1; SLC6A19)] and knockout mouse models have begun to reveal the basis of renal and intestinal reabsorption of amino acids in mammals.

Manuel Palacín (University of Barcelona Department of Biochemistry and Molecular Biology); Virginia Nunes (Institut de Recerca Oncològica Centre de Genètica Mèdica i Molecular); Mariona Font-Llitjós (Institut de Recerca Oncològica Centre de Genètica Mèdica i Molecular); Maite Jiménez-Vidal (University of Barcelona,Institut de Recerca Oncològica Department of Biochemistry and Molecular Biology,Centre de Genètica Mèdica i Molecular); Joana Fort (University of Barcelona Department of Biochemistry and Molecular Biology); Emma Gasol (University of Barcelona Department of Biochemistry and Molecular Biology)

2005-04-01

222

New Enzymatic Method of Chiral Amino Acid Synthesis by Dynamic Kinetic Resolution of Amino Acid Amides: Use of Stereoselective Amino Acid Amidases in the Presence of ?-Amino-?-Caprolactam Racemase?  

PubMed Central

d- and l-amino acids were produced from l- and d-amino acid amides by d-aminopeptidase from Ochrobactrum anthropi C1-38 and l-amino acid amidase from Pseudomonas azotoformans IAM 1603, respectively, in the presence of ?-amino-?-caprolactam racemase from Achromobacter obae as the catalyst by dynamic kinetic resolution of amino acid amides.

Yamaguchi, Shigenori; Komeda, Hidenobu; Asano, Yasuhisa

2007-01-01

223

Deduced amino acid sequence of human pulmonary surfactant proteolipid: SPL(pVal)  

SciTech Connect

Hydrophobic, proteolipid-like protein of Mr 6500 was isolated from ether/ethanol extracts of human, canine and bovine pulmonary surfactant. Amino acid composition of the protein demonstrated a remarkable abundance of hydrophobic residues, particularly valine and leucine. The N-terminal amino acid sequence of the human protein was determined: N-Leu-Ile-Pro-Cys-Cys-Pro-Val-Asn-Leu-Lys-Arg-Leu-Leu-Ile-Val4... An oligonucleotide probe was used to screen an adult human lung cDNA library and resulted in detection of cDNA clones with predicted amino acid sequence with close identity to the N-terminal amino acid sequence of the human peptide. SPL(pVal) was found within the reading frame of a larger peptide. SPL(pVal) results from proteolytic processing of a larger preprotein. Northern blot analysis detected in a single 1.0 kilobase SPL(pVal) RNA which was less abundant in fetal than in adult lung. Mixtures of purified canine and bovine SPL(pVal) and synthetic phospholipids display properties of rapid adsorption and surface tension lowering activity characteristic of surfactant. Human SPL(pVal) is a pulmonary surfactant proteolipid which may therefore be useful in combination with phospholipids and/or other surfactant proteins for the treatment of surfactant deficiency such as hyaline membrane disease in newborn infants.

Whitsett, J.A.; Glasser, S.W.; Korfhagen, T.R.; Weaver, T.E.; Clark, J.; Pilot-Matias, T.; Meuth, J.; Fox, J.L.

1987-05-01

224

Investigations of the clustering reactions of protonated amino acid esters by high pressure mass spectrometry and quantum chemical calculations  

NASA Astrophysics Data System (ADS)

The equilibria involved in the formation of the proton-bound dimers of the three simplest amino acid methyl esters (glycine, alanine and valine methyl esters) were characterized by means of pulsed ionization high pressure mass spectrometry (PHPMS) experiments and density functional theory (DFT) calculations. Our results would indicate that, within the temperature range employed in these experiments, the most stable proton-bound dimer conformers are formed in the case of glycine and alanine whereas a more entropically favoured isomer would dominate in the case of valine. Various possible isomers of each of the proton-bound dimer species have been investigated computationally each exhibiting a combination of inter- and intramolecular hydrogen bonding. A system of nomenclature for these various species is proposed. The possibility of structures exhibiting 'salt-bridge' interactions have also been explored, recognizing that such structures would necessarily result from highly energetic structural rearrangements.

Simon, A.; McMahon, T. B.

2006-09-01

225

Regulation of L-amino acid oxidase and of D-amino acid oxidase in Neurospora crassa  

Microsoft Academic Search

Neurospora crassa possesses an inducible L-amino acid oxidase that is expressed only when cells are derepressed for nitrogen in the presence of an amino acid. Enzyme synthesis requires both induction by an amino acid and simultaneous nitrogen catabolite derepression. Carbon limition in the presence of an amino acid does not permit induction of L-amino acid oxidase. The nit-2 gene is

Len Sikora; George A. Marzluf

1982-01-01

226

Differential diagnosis of (inherited) amino acid metabolism or transport disorders  

Microsoft Academic Search

Disorders of amino acid metabolism or transport are most clearly expressed in urine. Nevertheless the interpretation of abnormalities in urinary amino acid excretion remains difficult. An increase or decrease of almost every amino acid in urine can be due to various etiology. To differentiate between primary and secondary aminoacido-pathies systematic laboratory investigation is necessary. Early diagnosis of disorders of amino

W. Blom; J. G. M. Huijmans

1992-01-01

227

Regional amino acid transport into brain during diabetes: Effect of plasma amino acids  

SciTech Connect

Transport of phenylalanine and lysine into the brain was measured in 4-wk streptozotocin-diabetic rats to assess the effect on the neutral and basic amino acid transport systems at the blood-brain barrier. Amino acid concentrations in plasma and brain were also measured. Regional permeability-times-surface area (PS) products and influx were determined using a continuous infusion method and quantitative autoradiography. The PS of phenylalanine was decreased by an average of 40% throughout the entire brain. Influx was depressed by 35%. The PS of lysine was increased by an average of 44%, but the influx was decreased by 27%. Several plasma neutral amino acids (branched chain) were increased, whereas all basic amino acids were decreased. Brain tryptophan, phenylalanine, tyrosine, methionine, and lysine contents were markedly decreased. The transport changes were almost entirely accounted for by the alterations in the concentrations of the plasma amino acids that compete for the neutral and basic amino acid carriers. The reduced influx could be responsible for the low brain content of some essential amino acids, with possibly deleterious consequences for brain functions.

Mans, A.M.; DeJoseph, M.R.; Davis D.W.; Hawkins, R.A. (Pennsylvania State Univ. College of Medicine, Hershey (USA))

1987-11-01

228

Branched-chain amino acid metabolism in rat muscle: abnormal regulation in acidosis  

SciTech Connect

Branched-chain amino acid (BCAA) metabolism is frequently abnormal in pathological conditions accompanied by chronic metabolic acidosis. To study how metabolic acidosis affects BCAA metabolism in muscle, rats were gavage fed a 14% protein diet with or without 4 mmol NH/sub 4/Cl x 100 g body wt/sup -1/ x day/sup -1/. Epitrochlearis muscles were incubated with L-(1-/sup 14/C)-valine and L-(1-/sup 14/C)leucine, and rates of decarboxylation, net transamination, and incorporation into muscle protein were measured. Plasma and muscle BCAA levels were lower in acidotic rats. Rates of valine and leucine decarboxylation and net transamination were higher in muscles from acidotic rats; these differences were associated with a 79% increase in the total activity of branched-chain ..cap alpha..-keto acid dehydrogenase and a 146% increase in the activated form of the enzyme. They conclude that acidosis affects the regulation of BCAA metabolism by enhancing flux through the transaminase and by directly stimulating oxidative catabolism through activation of branched-chain ..cap alpha..-keto acid dehydrogenase.

May, R.C.; Hara, Y.; Kelly, R.A.; Block, K.P.; Buse, M.G.; Mitch, W.E.

1987-06-01

229

An amino acid transporter involved in gastric acid secretion  

Microsoft Academic Search

Gastric acid secretion is regulated by a variety of stimuli, in particular histamine and acetyl choline. In addition, dietary factors such as the acute intake of a protein-rich diet and the subsequent increase in serum amino acids can stimulate gastric acid secretion only through partially characterized pathways. Recently, we described in mouse stomach parietal cells the expression of the system

Philipp Kirchhoff; Mital H. Dave; Christine Remy; Ortrud Kosiek; Stephanie M. Busque; Matthias Dufner; John P. Geibel; Francois Verrey; Carsten A. Wagner

2006-01-01

230

Regulation of yeast acetohydroxyacid synthase by valine and ATP.  

PubMed Central

The first step in the common pathway for the biosynthesis of branched-chain amino acids is catalysed by acetohydroxyacid synthase (AHAS; EC 4.1.3.18). The enzyme is found in plants, fungi and bacteria, and is regulated by controls on transcription and translation, and by allosteric modulation of catalytic activity. It has long been known that the bacterial enzyme is composed of two types of subunit, and a similar arrangement has been found recently for the yeast and plant enzymes. One type of subunit contains the catalytic machinery, whereas the other has a regulatory function. Previously, we have shown [Pang and Duggleby (1999) Biochemistry 38, 5222--5231] that yeast AHAS can be reconstituted from its separately purified subunits. The reconstituted enzyme is inhibited by valine, and ATP reverses this inhibition. In the present work, we further characterize the structure and the regulatory properties of reconstituted yeast AHAS. High phosphate concentrations are required for reconstitution and it is shown that these conditions are necessary for physical association between the catalytic and regulatory subunits. It is demonstrated by CD spectral changes that ATP binds to the regulatory subunit alone, most probably as MgATP. Neither valine nor MgATP causes dissociation of the regulatory subunit from the catalytic subunit. The specificity of valine inhibition and MgATP activation are examined and it is found that the only effective analogue of either regulator of those tested is the non-hydrolysable ATP mimic, adenosine 5'-[beta,gamma-imido]triphosphate. The kinetics of regulation are studied in detail and it is shown that the activation by MgATP depends on the valine concentration in a complex manner that is consistent with a proposed quantitative model.

Pang, S S; Duggleby, R G

2001-01-01

231

Metabolism of the amino acid beta-pyrazol-1-ylalanine and its parent base pyrazole.  

PubMed

beta-Pyrazol-1-yl-DL-alanine, an uncommon amino acid from plants of the Cucurbitaceae, was fed to mice. Although pyrazole is known to affect the liver enzymes UDP-glucose dehydrogenase, UDP-glucuronyl transferase and UDP-glucuronic acid pyrophosphatase, and also depresses their liver glycogen concentrations, beta-pyrazol-1-ylalanine had no such effects. beta-Pyrazol-1-ylalanine could not be detected in the liver of the experimental animals but was present in the urine. No other change in urinary amino acid content was observed. Studies with [14C]-beta-pyrazol-1-yl-DL-alanine showed the administered amino acid was excreted over a 4-day period, 93% of the compound supplied was recovered. Similar recoveries were obtained with the L-enantiomer from cucumber seed. The metabolic inertness of beta-pyrazol-1-ylalanine was also apparent in experiments involving subcutaneous injection of this compound. Administration of pyrazole confirmed an earlier report of resultant increased activity of liver UDP-glucose dehydrogenase and UDP-glucuronyl transferase, and of the depression of activity of liver UDP-glucuronic acid pyrophosphatase. A concomitant 40% decrease in liver glycogen content was seen. The urine contained a novel metabolite, identified as a peptide conjugate of a pyrazole derivative. Mass spectrometry and p.m.r. spectroscopy indicate that this derivative is 3,4,4-trimethyl-5-pyrazolone. The amino acid constituents are aspartic acid, threonine, serine, glutamic acid, proline, glycine, alanine, valine and leucine. The urine of mice receiving pyrazole contained less free glycine and alanine than controls. From the results, it is concluded that pyrazole is not a catabolite of dietary beta-pyrazol-1-ylalanine but to the contrary, the amino acid is essentially excreted unchanged. Formation of 3,4,4-trimethyl-5-pyrazolone from pyrazole would imply C-methylation, a process that has not been previously observed in a mammalian detoxication context. PMID:2986641

Al-Baldawi, N F; Brown, E G

1985-04-15

232

Polymerization of amino acids containing nucleotide bases  

NASA Technical Reports Server (NTRS)

The nucleoamino acids 1-(3'-amino,3'-carboxypropyl)uracil (3) and 9-(3'-amino,3'-carboxypropyl)adenine (4) have been prepared as (L)-en-antiomers and as racemic mixtures. When 3 or 4 is suspended in water and treated with N,N'-carbon-yldiimidazole, peptides are formed in good yield. The products formed from the (L)-enantiomers are hydrolyzed to the monomeric amino acids by pronase. Attempts to improve the efficiency of these oligomerizations by including a polyuridylate template in the reaction mixture were not successful. Similarly, oligomers derived from the (L)-enantiomer of 3 did not act as templates to facilitate the oligomerization of 4.

Ben Cheikh, Azzouz; Orgel, Leslie E.

1990-01-01

233

Branched-chain amino acids alleviate nonalcoholic steatohepatitis in rats.  

PubMed

Nonalcoholic steatohepatitis (NASH) is a prevalent disease in countries around the world. The branched-chain amino acids (BCAAs) leucine, isoleucine, and valine cannot be synthesized by the body and have been shown to promote muscle buildup; thus, it is logical to suggest that BCAAs can reduce fat deposition in the body. We used gonadectomized rats fed a high-fat diet to investigate the effects of BCAAs on lipid metabolism over an 8-week experimental period. Body composition, tissue histology, plasma lipid indices, and hormone levels were examined. We demonstrated that the body weights of rats were not significantly decreased but the mesenteric fat was significantly decreased (p < 0.05) in BCAA-treated rats. In addition, BCAAs decreased plasma lipid levels and fat deposition in the liver. At week 4, when the untreated rats displayed macrovesicular steatosis, BCAA-treated rats had only macrovesicular droplets in their hepatocytes. At week 8, when the untreated rat livers displayed profound inflammation and cirrhosis, BCAA-treated rat livers remained in the macrovesicular stage of steatosis. BCAAs induced higher blood glucose and plasma insulin levels (p < 0.05). BCAAs also improved liver blood flow by increasing mean arterial blood pressure and decreasing portal pressure, which helped delay the change in blood flow pattern to that of cirrhosis. BCAAs also induced the skeletal muscle to express higher levels of branched-chain ?-keto acid dehydrogenase E1?, which indicates an enhanced metabolic capacity of BCAAs in muscle tissue. This study clearly demonstrates the effects of BCAAs on the amelioration of fat deposition in rats fed a high-fat diet. PMID:23855271

Li, Tianrun; Geng, Leiluo; Chen, Xin; Miskowiec, Miranda; Li, Xuan; Dong, Bing

2013-08-01

234

Structual comparison of dermatopontin amino acid sequences  

Microsoft Academic Search

Dermatopontin is a tyrosine-rich acidic extracellular matrix protein of 22 kD with possible functions in cellmatrix interactions\\u000a and matrix assembly. Database of GenBank+EMBL+DDBJ sequences from Nucleotide, Gene, and Expressed Sequence Tag (EST) Divisions\\u000a was searched with a keyword “dermatopontin” or mouse dermatopontin amino acid sequence. In addition to five mammals previously\\u000a described, five mammalian, two bird, one fish dermatopontin genes

Takumi Takeuchi

2010-01-01

235

Protein tolerance to random amino acid change  

Microsoft Academic Search

Mutagenesis of protein-encoding sequences occurs ubiquitously; it enables evolution, accumulates during aging, and is associated with disease. Many biotechnological methods exploit random mutations to evolve novel proteins. To quantitate protein tolerance to random change, it is vital to understand the probability that a random amino acid replacement will lead to a protein's functional inactivation. We define this probability as the

Haiwei H. Guo; Juno Choe; Lawrence A. Loeb

2004-01-01

236

Phenylketonuria: Defects in Amino Acid Metabolism  

Microsoft Academic Search

Phenylketonuria (PKU) is the most common disorder of amino acid metabolism affecting the PAH gene, which encodes for the enzyme phenylalanine hydroxylase. This defect results in toxic hyperphenylalanemia from a breakdown in the hydroxylation of phenylalanine (Phe) to tyrosine, the first step in the catabolic metabolism of Phe. This defect causes the symptoms of PKU, which include profound mental retardation

Matthew Madden

237

Aromatic amino acid hydroxylase genes and schizophrenia  

Microsoft Academic Search

Phenylalanine hydroxylase (PAH), which catalyzes the conversion of phenylalanine to tyrosine, shares physical, structural and catalytic properties with tyrosine hydroxy- lase (TH) and tryptophan hydroxylase (TPH) that catalyze the rate-limiting steps in the biosynthesis of the neurotransmitters dopa- mine, noradrenaline, and serotonin. Be- cause these neurotransmitter systems have all been implicated in the pathophysiology of schizophrenia, the aromatic amino acid

Helen M. Chao; Mary Ann Richardson

2002-01-01

238

High-pressure polymorphism in amino acids  

Microsoft Academic Search

Pressure up to 10 GPa is a powerful method for studying polymorphism in organic crystal structures, and this review surveys work carried out on high-pressure polymorphism in amino acids. High-pressure polymorphs have been established crystallographically for glycine, alanine, serine, cysteine and leucine. Phase transitions can be driven by the avoidance of very short intermolecular contacts or by promotion of a

Stephen A. Moggach; Simon Parsons; Peter A. Wood

2008-01-01

239

Enantioenrichment in sublimed amino acid mixtures.  

PubMed

A real amplification of an initial enantiomeric excess can be detected when two amino acids are sublimed at high temperature, even if one of the components is a racemic compound that does not convert into a conglomerate by sublimation. PMID:22388769

Viedma, Cristóbal; Ortiz, José E; de Torres, Trinidad; Cintas, Pedro

2012-04-14

240

Amino Acid Sequence of Human Cholinesterase.  

National Technical Information Service (NTIS)

The active site serine residue is located 198 amino acids from the N-terminal. The active site peptide was isolated from three different genetic types of human serum cholinesterase: from usual, atypical, and atypical-silent genotypes. It was found that th...

O. Lockridge

1985-01-01

241

Amino Acid Formation on Interstellar Dust Particles  

NASA Astrophysics Data System (ADS)

In the dense interstellar medium dust particles accrete ice layers of known molecular composition. In the diffuse interstellar medium these ice layers are subjected to energetic UV-irradiation. Here, photoreactions form complex organic molecules. The interstellar processes were recently successfully simulated in two laboratories. At NASA Ames Research Center three amino acids were detected in interstellar ice analogues [1], contemporaneously, our European team reported on the identification of 16 amino acids therein [2]. Amino acids are the molecular building blocks of proteins in living organisms. The identification of amino acids on the simulated icy surface of interstellar dust particles strongly supports the assumption that the precursor molecules of life were delivered from interstellar and interplanetary space via (micro-) meteorites and/or comets to the earyl Earth. The results shall be verified by the COSAC experiment onboard the ESA cometary mission Rosetta [3]. [1] M.P. Bernstein, J.P. Dworkin, S.A. Sandford, G.W. Cooper, L.J. Allamandola: itshape Nature \\upshape 416 (2002), 401-403. [2] G.M. Muñoz Caro, U.J. Meierhenrich, W.A. Schutte, B. Barbier, A. Arcones Sergovia, H. Rosenbauer, W.H.-P. Thiemann, A. Brack, J.M. Greenberg: itshape Nature \\upshape 416 (2002), 403-406. [3] U. Meierhenrich, W.H.-P. Thiemann, H. Rosenbauer: itshape Chirality \\upshape 11 (1999), 575-582.

Meierhenrich, U. J.; Munoz Caro, G. M.; Barbier, B.; Brack, A.; Thiemann, W.; Goesmann, F.; Rosenbauer, H.

2003-04-01

242

Compartmentalization of amino acids in surfactant aggregates - Partitioning between water and aqueous micellar sodium dodecanoate and between hexane and dodecylammonium propionate trapped water in hexane  

NASA Technical Reports Server (NTRS)

The partitioning of amino acids (glycine, alanine, leucine, phenylalanine, histidine, aspartic acid, glutamic acid, lysine, isoleucine, threonine, serine, valine, proline, arginine) in aqueous and nonaqueous micellar systems was studied experimentally. Partitioning from neat hexane into dodecylammonium propionate trapped water in hexane was found to be dependent on both electrostatic and hydrophobic interactions, which implies that the interior of dodecylammonium propionate aggregates is negatively charged and is capable of hydrogen bonding in addition to providing a hydrophobic environment. Unitary free energies of transfer of amino acid side chains from hexane to water were determined and solubilities of amino acids in neat hexane substantiated the amino acid hydrophobicity scale. The relevance of the experiments to prebiotic chemistry was examined.

Fendler, J. H.; Nome, F.; Nagyvary, J.

1975-01-01

243

Chemo-enzymatic synthesis of isotopically labelled L-Valine, L-Isoleucine and allo-isoleucine  

Microsoft Academic Search

Syntheses of (3R)-[4,4,4-D3]-L-valine, [15N]-L-isoleucine and [15N]-allo-isoleucine from homochiral 2-alkylated carboxylic acids are described. The approach involves a one-carbon homologation of the carboxylic acid to give the corrresponding ?-substituted ?-keto ester which is converted directly to the ?-amino acid in a one-pot procedure involving two enzyme catalysed reactions (Candida cylindracea lipase to hydroluse the ester and leucine dehydrogenase to catalyse the

Nicholas M. Kelly; R. Gordon Reid; Christine L. Wellis; Peter L. Winton

1996-01-01

244

Amino Acid Metabolism of Pea Leaves  

PubMed Central

In the young leaves of pea (Pisum sativum L.) plants, there was a diurnal variation in the levels of amino acids. In the light, total amino nitrogen increased for the first few hours, then stabilized; in the dark, there was a transient decrease followed by a gradual recovery. Asparagine, homoserine, alanine, and glutamine accounted for much of these changes. The incorporation of 15N into various components of the young leaves was followed after supply of 15N-nitrate. 15N appeared most rapidly in ammonia, due to reduction in the leaf, and this process took place predominantly in the light. A large proportion of the primary assimilation took place through the amide group of glutamine, which became labeled and turned over rapidly; labeling of glutamic acid and alanine was also rapid. Asparagine (amide group) soon became labeled and showed considerable turnover. Slower incorporation and turnover were found for aspartic acid, ?-aminobutyric acid, and homoserine. Synthesis and turnover of all of the amino acids continued at a low rate in the dark. ?-Aminobutyric acid was the only compound found to label more rapidly in the dark than in the light.

Bauer, Alfred; Urquhart, Aileen A.; Joy, Kenneth W.

1977-01-01

245

D-Amino Acids in Living Higher Organisms  

NASA Astrophysics Data System (ADS)

The homochirality of biological amino acids (L-amino acids) and of the RNA/DNA backbone (D-ribose) might have become established before the origin of life. It has been considered that D-amino acids and L-sugars were eliminated on the primitive Earth. Therefore, the presence and function of D-amino acids in living organisms have not been studied except for D-amino acids in the cell walls of microorganisms. However, D-amino acids were recently found in various living higher organisms in the form of free amino acids, peptides, and proteins. Free D-aspartate and D-serine are present and may have important physiological functions in mammals. D-amino acids in peptides are well known as opioid peptides and neuropeptides. In protein, D-aspartate residues increase during aging. This review deals with recent advances in the study of D-amino acids in higher organisms.

Fujii, Noriko

2002-04-01

246

Effects of amino acids administered to a perfused area of the skin in Angora goats.  

PubMed

The effect of infusion of supplemental amino acids on growth of mohair by Angora goats was investigated using a skin perfusion model. Four Angora wethers (average BW 32 +/- 2 kg) were implanted bilaterally with silicon catheters into the superficial branches of the deep circumflex iliac artery and vein. For the first 14 d of the experiment, goats were arterially infused with either a mixture of amino acids (one side) or saline (contralateral side). The hourly infusion rates of amino acids were .36 mg of methionine, .36 mg of lysine, and .72 mg of leucine. The area of skin supplied by the deep circumflex iliac artery was approximately 300 cm2; a tattoo 10 cm x 15 cm was made in the middle of the perfused region for quantifying mohair production and characteristics. Two weeks after cessation of infusions goats were shorn and the mohair from the tattooed regions was examined. Greasy and clean mohair production from the tattooed region were increased by amino acid infusion compared with the contralateral side infused with saline (3.51 vs 3.16 g, P < .04 and 3.13 vs 2.70 g, P < .07, respectively). Although mohair length and diameter were not significantly altered, venous concentrations of valine, threonine, arginine, glycine, and histidine were decreased by infusion of the amino acids (P < .05), no differences in T3, T4, or insulin concentrations in venous blood were detected, but plasma cortisol concentration was reduced (1.38 vs 2.61 micrograms/dL, P < .05) with amino acid infusion.(ABSTRACT TRUNCATED AT 250 WORDS) PMID:7601791

Pucha?a, R; Sahlu, T; Pierzynowski, S G; Hart, S P

1995-02-01

247

Brain-blood amino acid correlates following protein restriction in murine maple syrup urine disease  

PubMed Central

Background Conventional therapy for patients with maple syrup urine disease (MSUD) entails restriction of protein intake to maintain acceptable levels of the branched chain amino acid, leucine (LEU), monitored in blood. However, no data exists on the correlation between brain and blood LEU with protein restriction, and whether correction in blood is reflected in brain. Methods To address this question, we fed intermediate MSUD mice diets of 19% (standard) and 6% protein, with collection of sera (SE), striata (STR), cerebellum (CE) and cortex (CTX) for quantitative amino acid analyses. Results LEU and valine (VAL) levels in all brain regions improved on average 28% when shifting from 19% to 6% protein, whereas the same improvements in SE were on average 60%. Isoleucine (ILE) in brain regions did not improve, while the SE level improved 24% with low-protein consumption. Blood-branched chain amino acids (LEU, ILE, and VAL in sera (SE)) were 362-434 ?M, consistent with human values considered within control. Nonetheless, numerous amino acids in brain regions remained abnormal despite protein restriction, including glutamine (GLN), aspartate (ASP), glutamate (GLU), gamma-aminobutyric acid (GABA), asparagine (ASN), citrulline (CIT) and serine (SER). To assess the specificity of these anomalies, we piloted preliminary studies in hyperphenylalaninemic mice, modeling another large neutral aminoacidopathy. Employing an identical dietary regimen, we found remarkably consistent abnormalities in GLN, ASP, and GLU. Conclusions Our results suggest that blood amino acid analysis may be a poor surrogate for assessing the outcomes of protein restriction in the large neutral amino acidopathies, and further indicate that chronic neurotransmitter disruptions (GLU, GABA, ASP) may contribute to long-term neurocognitive dysfunction in these disorders.

2014-01-01

248

Metabolic effects of inhibitors of two enzymes of the branched-chain amino acid pathway in Salmonella typhimurium.  

PubMed Central

The metabolic effects of inhibitors of two enzymes in the pathway for biosynthesis of branched-chain amino acids were examined in Salmonella typhimurium mutant strain TV105, expressing a single isozyme of acetohydroxy acid synthase (AHAS), AHAS isozyme II. One inhibitor was the sulfonylurea herbicide sulfometuron methyl (SMM), which inhibits this isozyme and AHAS of other organisms, and the other was N-isopropyl oxalylhydroxamate (IpOHA), which inhibits ketol-acid reductoisomerase (KARI). The effects of the inhibitors on growth, levels of several enzymes of the pathway, and levels of intermediates of the pathway were measured. The intracellular concentration of the AHAS substrate 2-ketobutyrate increased on addition of SMM, but a lack of correlation between increased ketobutyrate and growth inhibition suggests that the former is not the immediate cause of the latter. The levels of the keto acid precursor of valine, but not of the precursor of isoleucine, were drastically decreased by SMM, and valine, but not isoleucine, partially overcame SMM inhibition. This apparent stronger effect of SMM on the flux into the valine arm, as opposed to the isoleucine arm, of the branched-chain amino acid pathway is explained by the kinetics of the AHAS reaction, as well as by the different roles of pyruvate, ketobutyrate, and the valine precursor in metabolism. The organization of the pathway thus potentiates the inhibitory effect of SMM. IpOHA has strong initial effects at lower concentrations than does SMM and leads to increases both in the acetohydroxy acid substrates of KARI and, surprisingly, in ketobutyrate. Valine completely protected strain TV105 from IpOHA at the MIC. A number of explanations for this effect can be ruled out, so that some unknown arrangement of the enzymes involved must be suggested. IpOHA led to initial cessation of growth, with partial recovery after a time whose duration increased with the inhibitor concentration. The recovery is apparently due to induction of new KARI synthesis, as well as disappearance of IpOHA from the medium.

Epelbaum, S; Chipman, D M; Barak, Z

1996-01-01

249

Role of rhizobial biosynthetic pathways of amino acids, nucleotide bases and vitamins in symbiosis.  

PubMed

Rhizobia require the availability of 20 amino acids for the establishment of effective symbiosis with legumes. Some of these amino acids are synthesized by rhizobium, whereas the remaining are supplied by the host plant. The supply from plant appears to be plant-type specific. Alfalfa provides arginine, cysteine, isoleucine, valine and tryptophan, and cowpea and soybean provide histidine. The production of ornithine and anthranilic acid, the intermediates in the biosynthetic pathways of arginine and tryptophan, respectively, seems to be essential for effective symbiosis of Sinorhizobium meliloti with alfalfa. The expression of ilvC gene of S. meliloti is required for induction of nodules on the roots of alfalfa plants. An undiminished metabolic flow through the rhizobial pathways for the synthesis of purines and pyrimidines and the synthesis of biotin, nicotinic acid, riboflavin and thiamine by rhizobium appear to be requirements for normal symbiosis. To the best of our knowledge, this is the first review article on the role of rhizobial biosynthetic pathways of amino acids, nucleotide bases and vitamins in rhizobium-legume symbiosis. The scientific developments of about 35 years in this field have been reviewed. PMID:12597544

Randhawa, Gursham S; Hassani, Raad

2002-07-01

250

Sequential injection chromatography for fluorimetric determination of intracellular amino acids in marine microalgae.  

PubMed

This chapter describes a sequential injection chromatography method to automate the fluorimetric determination of amino acids after precolumn derivatization with o-phthaldialdehyde in presence of 2-mercaptoethanol using reverse-phase liquid chromatography in C(18) silica-based monolithic column. The method is low-priced and based on six steps of isocratic elutions. At a flow rate of 30 ?l/s, a 25 mm long-column coupled to 5-mm guard column is capable to separate aspartic acid (Asp), glutamic acid (Glu), asparagine (Asn), serine (Ser), glycine (Gly), threonine (Thr), citrulline (Ctr), arginine (Arg), alanine (Ala), tyrosine (Tyr), phenylalanine (Phe), ornithine (Orn), and lysine (Lys). Under these conditions, histidine (His) and glutamine (Gln), methionine (Met) and valine (Val), and isoleucine (Ile) and leucine (Leu) coelute. The entire cycle of amino acids derivatization, chromatographic separation, and column conditioning at the end of separation lasts 16 min. The method was successfully applied to the determination of the major intracellular free amino acids in the marine green alga Tetraselmis gracilis. PMID:22125154

Rigobello-Masini, Marilda; Masini, Jorge C

2012-01-01

251

Gas-phase acidities of the 20 protein amino acids  

NASA Astrophysics Data System (ADS)

The gas-phase acidities of the 20 protein amino acids (PAAs) have been determined using an electrospray ionization-quadrupole ion trap instrument. Three different methods were used to determine both the absolute acidities and the relative acidity ordering of the PAAs. The extended kinetic method was used to determine absolute acidities for all 20 PAAs with substituted carboxylic acids and substituted phenols as reference acids. Acidities were obtained with an average uncertainty of ±10 kJ/mol, which is large compared to some of the differences between amino acids with similar acidities. To determine the relative acidity ordering, single-reference kinetic method experiments were performed using both the reference acids from the absolute acidity studies and tryptophan and threonine as reference acids. Additional ordering information was obtained from kinetic method experiments in which proton-bound dimer ions comprising pairs of amino acids were generated and dissociated in the ion trap. The recommended acidity ordering is Gly < Ala < Pro < Val < Leu < Ile < Lys < Trp < Phe < Tyr < Met < Ser < Thr < Cys < Gln < Gln < Arg < Asn < His < Glu < Asp. Isodesmic acidity values were also obtained at the B3LYP/6-311++G**//B3LYP/6-31+G* level of theory with acetic acid as the reference acid. The theoretical acidities are in excellent agreement with the absolute acidities obtained from the extended kinetic method studies. The calculations predict that the preferred isomer for protonated cysteine and tyrosine is not a carboxylate anion, but rather a thiolate anion and a phenoxide anion, respectively.

Jones, Christopher M.; Bernier, Matthew; Carson, Erin; Colyer, Kathryn Ee; Metz, Rachel; Pawlow, Anna; Wischow, Emily D.; Webb, Ian; Andriole, Erica J.; Poutsma, John C.

2007-11-01

252

Evolution from amino acids - Lunar occurrence of their precursors.  

NASA Technical Reports Server (NTRS)

Review of the present state of experimentally based concepts of organic evolution from amino acids. Earlier studies of the synthesis of amino acid precursors from meteoritic material, lunar dust, and terrestrial lava are briefly summarized, and laboratory experiments in which polymers of amino acids were obtained either by direct heating of dry amino acids or by heating aqueous solutions of mixtures of amino acids are described. In particular, a process is described by which alpha-amino acids were made to react to form linear chains of proteinoids. It is concluded that a proteinoid microsystem was a common ancestor of all life on earth.

Fox, S. W.

1972-01-01

253

Chemical Properties of Amino Acids and Identification of Unknown Amino Acids  

NSDL National Science Digital Library

This resource describes two related laboratory exercises on the chemical properties and identification of amino acids (the building blocks of proteins). Detailed pre-lab assignments and guidelines for students' laboratory reports are provided.

Karen Sprague (University of Oregon;); Carl Stiefbold (University of Oregon;); Sam Donovan (University of Oregon;)

1996-01-01

254

[Secretion of endogenous amino acids in the gastrointestinal tract and amino acid resorption in the swine].  

PubMed

A trial was performed with 2 fistula pigs (each with 2 fistulas, one located about 30 cm below the pyloric orifice and the other at the end of the small intestine). Animal A received a casein diet containing 14% crude protein for a period of 2 weeks before the tracer amino acid was administered. Animal B received the same diet for a period of 10 days and was then fed a diet (at the same protein level) containing gluten as sole protein source. The two tracer amino acids, 14C-U-L-leucine and 3H-4,5-(N)-L-lysine, were injected intravenously. The passage rates for dry matter, organic matter and N measured at the beginning of the small intestine were higher than the rate of intake. The rate of passage of amino acids was also found to be increased relative to the rate of intake. In general, this increase involved the non-essential amino acids to a much larger extent. A considerable proportion of the amino acids passing into the large intestine is not excreted with the faeces but is probably converted in catabolic processes. It is for this reason that any values for the efficiency of amino acid absorption calculated on the basis of data on the faecal excretion of amino acids will not provide conclusive evidence for the availability of dietary amino acids in processes of the intermediate metabolism. The rate of secretion of 3H and 14C radioactivity into the digesta of the small intestine was found to increase rapidly within 1-2 hrs after administration of the tracer amino acids. The 14C radioactivity detected was found to be almost exclusively derived from 14C leucine while only about 60% of the 3H activity found in the digesta of fistula I were shown to be bound to lysine. Labelled lysine and leucine (of endogenic origin) are absorbed into the small intestine at a slower rate (i.e. endogenic proteins are less efficiently digested) than the non-radioactive amino acids (of exogenic origin) so that a process of concentration of endogenic amino acids is observed towards the end of the small intestine. PMID:962584

Zebrowska, T; Simon, O; Münchmeyer, R; Bergner, H

1976-02-01

255

Postcolumn co-immobilized leucine dehydrogenase-NADH oxidase reactor for the determination of branched-chain amino acids by high-performance liquid chromatography with chemiluminescence detection  

Microsoft Academic Search

A liquid chromatographic system with a co-immobilized leucine dehydrogenase-NADH oxidase reactor is described for the determination of branched-chain amino acids such as l-leucine, l-isoleucine and l-valine. The enzymes were simultaneously immobilized on tresylate-containing poly(vinyl alcohol) beads. The separation was achieved by means of an ODS column with elution with phosphate buffer (pH 7.5). The hydrogen peroxide produced was detected chemiluminometrically

Nobutoshi Kiba; Yukio Oyama; Akira Kato; Motohisa Furusawa

1996-01-01

256

Effects of aspartame and glucose administration on brain and plasma levels of large neutral amino acids and brain 5-hydroxyindoles14  

Microsoft Academic Search

Administration of the artificial sweetener aspartame (L-aspartylphenylalanyl- methyl ester, 200 mg\\/kg) by gavage to rats caused large increments in brain and plasma levels of phenylalanine and its product tyrosine. Glucose administration (3 g\\/kg, by gavage, a dose sufficient to cause insulin-mediated reductions in plasma levels of the large neutral amino acids leucine, isoleucine, and valine) also elevated brain phenylalanine and

Hidehiko Yokogoshi; Carolyn H Roberts; Benjamin Caballero; Richard J Wurtman

257

Alterations in protein metabolism and amino acid concentrations in rats fed by a high-protein (casein-enriched) diet – Effect of starvation  

Microsoft Academic Search

Rats were fed with a standard laboratory diet (SLD) or a high-protein diet (HPD). After three months changes in amino acid concentration and protein metabolism were examined in fed and 24h-fasted animals. In the blood of the HPD animals sacrificed in fed state were found higher concentrations of urea, aspartate, taurine, proline, valine, isoleucine, and leucine, and lower concentrations of

Milan Holecek; Miroslav Kovarik

2011-01-01

258

Resolution of enantiomers of DL-amino acids on silica gel plates impregnated with optically pure (-)-quinine.  

PubMed

TLC resolution of enantiomers from racemic amino acids was achieved on silica gel plates impregnated with optically pure (-)-quinine. The successful solvent systems were butanol-chloroform-acetic acid (3:7:5, v/v) for DL-methionine; 6:8:4, v/v for alanine; 10:1:4; v/v for threonine; and ethyl acetate-carbon tetrachloride-propionic acid (10.5:6.5:3.5, v/v) for valine. Minimum detection limits were found to be different for each of the amino acid, ranging between 0.9 and 3.7 microg. The effects of concentration of impregnating reagent, temperature and pH on resolution of enantiomers have been studied in details. PMID:11746238

Bhushan, R; Arora, M

2001-11-01

259

Thin-Layer Separation of Citric Acid Cycle Intermediates, Lactic Acid, and the Amino Acid Taurine.  

National Technical Information Service (NTIS)

This paper describes a two-dimensional mixed-layer method for separating citric acid cycle intermediates, lactic acid and the amino acid taurine. The method cleanly separates all citric acid cycle intermediates tested, excepting citric acid and isocitric ...

R. T. Riley M. C. Mix

1979-01-01

260

Regional amino acid transport into brain during diabetes: Effect of plasma amino acids  

Microsoft Academic Search

Transport of phenylalanine and lysine into the brain was measured in 4-wk streptozotocin-diabetic rats to assess the effect on the neutral and basic amino acid transport systems at the blood-brain barrier. Amino acid concentrations in plasma and brain were also measured. Regional permeability-times-surface area (PS) products and influx were determined using a continuous infusion method and quantitative autoradiography. The PS

A. M. Mans; M. R. DeJoseph; Davis D. W; R. A. Hawkins

1987-01-01

261

Permeability of membranes to amino acids and modified amino acids: mechanisms involved in translocation  

NASA Technical Reports Server (NTRS)

The amino acid permeability of membranes is of interest because they are one of the key solutes involved in cell function. Membrane permeability coefficients (P) for amino acid classes, including neutral, polar, hydrophobic, and charged species, have been measured and compared using a variety of techniques. Decreasing lipid chain length increased permeability slightly (5-fold), while variations in pH had only minor effects on the permeability coefficients of the amino acids tested in liposomes. Increasing the membrane surface charge increased the permeability of amino acids of the opposite charge, while increasing the cholesterol content decreased membrane permeability. The permeability coefficients for most amino acids tested were surprisingly similar to those previously measured for monovalent cations such as sodium and potassium (approximately 10(-12)-10(-13) cm s-1). This observation suggests that the permeation rates for the neutral, polar and charged amino acids are controlled by bilayer fluctuations and transient defects, rather than partition coefficients and Born energy barriers. Hydrophobic amino acids were 10(2) more permeable than the hydrophilic forms, reflecting their increased partition coefficient values. External pH had dramatic effects on the permeation rates for the modified amino acid lysine methyl ester in response to transmembrane pH gradients. It was established that lysine methyl ester and other modified short peptides permeate rapidly (P = 10(-2) cm s-1) as neutral (deprotonated) molecules. It was also shown that charge distributions dramatically alter permeation rates for modified di-peptides. These results may relate to the movement of peptides through membranes during protein translocation and to the origin of cellular membrane transport on the early Earth.

Chakrabarti, A. C.; Deamer, D. W. (Principal Investigator); Miller, S. L. (Principal Investigator)

1994-01-01

262

Determining important regulatory relations of amino acids from dynamic network analysis of plasma amino acids  

Microsoft Academic Search

The changes in the concentrations of plasma amino acids do not always follow the flow-based metabolic pathway network. We\\u000a have previously shown that there is a control-based network structure among plasma amino acids besides the metabolic pathway\\u000a map. Based on this network structure, in this study, we performed dynamic analysis using time-course data of the plasma samples\\u000a of rats fed

Nahoko Shikata; Yukihiro Maki; Masahiko Nakatsui; Masato Mori; Yasushi Noguchi; Shintaro Yoshida; Michio Takahashi; Nobuo Kondo; Masahiro Okamoto

2010-01-01

263

Evidence for valine intolerance in patients with cirrhosis.  

PubMed

Valine (62.5 mg per kg), leucine (70 mg per kg) and equal amounts of the calcium salts of the corresponding keto acids, i.e., alpha-ketoisovaleric acid (KIVA) and alpha-ketoisocaproic acid (KICA) were orally administered to patients with cirrhosis and to control subjects. Valine or leucine ingestion increased serum valine and leucine levels and the corresponding keto acids, KIVA and KICA, in cirrhotics and controls. KIVA or KICA ingestion increased serum KIVA and KICA concentrations within a few minutes associated with a rise in valine and leucine. In cirrhotics, administration of valine or KIVA resulted in significantly higher serum valine or KIVA concentrations than in control subjects. The clearance of valine and KIVA from blood was also delayed in cirrhotic patients. No such differences were observed after leucine or KICA ingestion. It is suggested that cirrhotics have a diminished tolerance for valine. Since the tolerance for KIVA, but not KICA, is also impaired, it appears that cirrhotics have a derangement in one or more metabolic steps distal to the branched-chain keto acid dehydrogenase. PMID:6745855

Schauder, P; Schröder, K; Herbertz, L; Langer, K; Langenbeck, U

1984-01-01

264

Beneficial effects of l-leucine and l-valine on arrhythmias, hemodynamics and myocardial morphology in rats.  

PubMed

Branched chain amino acids (BCAA) have been shown to have a general protective effect on the heart in different animal models as well as in humans. However, so far no attempt has been made to specifically elucidate their influence on arrhythmias. Our study was performed to evaluate whether an infusion of either l-leucine or l-valine in a dose of 1mgkg(-1)h(-1) 10min before a 7-min period of left anterior descending artery occlusion followed by 15min of reperfusion, had an effect on arrhythmias measured during the reperfusion phase in the ischemia- and reperfusion-induced arrhythmias model in rats in vivo. The effect of the infusion of these substances on mean arterial blood pressure was monitored throughout the experiment. Both of the tested amino acids exhibited significant antiarrhythmic properties. l-Leucine reduced the duration of ventricular fibrillation (P<0.05) and l-valine decreased the duration of ventricular fibrillation (P<0.001) and ventricular tachycardia (P<0.05). The two amino acids were generally hypotensive. l-Valine lowered blood pressure in all phases of the experiment (P<0.05) while l-leucine lowered this parameter mainly towards the end of occlusion and reperfusion (P<0.05). In addition, 30min infusion of the amino acids in the used dose did not produce any apparent adverse histological changes that were remarkably different from control. In summary, the results of our study suggest that l-leucine and l-valine in the dose that was used attenuates arrhythmias and are hypotensive in their influence. Our findings lend support to the many ongoing investigations into the benefit of the application of l-leucine and l-valine in cardiology like their addition to cardioplegic solutions. PMID:21605982

Mitr?ga, Katarzyna; Zorniak, Micha?; Varghese, Benoy; Lange, Dariusz; No?ynski, Jerzy; Porc, Maurycy; Bia?ka, Szymon; Krzemi?ski, Tadeusz F

2011-09-01

265

Amino acids of the Murchison meteorite. I - Six carbon acyclic primary alpha-amino alkanoic acids  

NASA Technical Reports Server (NTRS)

Six of the seven chain isomers of six-carbon acyclic primary alpha-amino alkanoic acids (leucine isomers) have been either identified or confirmed in hot-water extracts of the Murchison meteorite using combined gas chromatography-mass spectrometry (GC-MS) and ion exchange chromatography. 2-Amino-2-ethylbutyric acid, 2-amino-2,3-dimethylbutyric acid, pseudoleucine, and 2-methylnorvaline were positively identified by GC-MS. These amino acids have not been previously reported to occur in natural materials and may be uniquely meteoritic in origin. The presence of leucine and isoleucine (including the diastereoisomer, alloisoleucine) was confirmed. Peaks corresponding to norleucine were seen by ion-exchange and gas chromatography but characteristic mass spectra were not obtained. The alpha-branched chain isomers in this series are quantitatively the most significant. These results are compared with literature data on amino acid synthesis by electrical discharge and Fischer-Tropsch-type catalysis. Neither model system produces an amino acid suite that is completely comparable to that found in the Murchison meteorite.

Cronin, J. R.; Gandy, W. E.; Pizzarello, S.

1981-01-01

266

Amino acids of the Murchison meteorite: I. Six carbon acyclic primary alpha-amino alkanoic acids.  

PubMed

Six of the seven chain isomers of six-carbon acyclic primary alpha-amino alkanoic acids (leucine isomers) have been either identified or confirmed in hot-water extracts of the Murchison meteorite using combined gas chromatography-mass spectrometry (GC-MS) and ion exchange chromatography. 2-Amino-2-ethylbutyric acid, 2-amino-2,3-dimethylbutyric acid, pseudoleucine, and 2-methylnorvaline were positively identified by GC-MS. These amino acids have not been previously reported to occur in natural materials and may be uniquely meteoritic in origin. The presence of leucine and isoleucine (including the diastereoisomer, alloisoleucine) was confirmed. Peaks corresponding to norleucine were seen by ion-exchange and gas chromatography but characteristic mass spectra were not obtained. The alpha-branched chain isomers in this series are quantitatively the most significant. These results are compared with literature data on amino acid synthesis by electrical discharge and Fischer-Tropsch-type catalysis. Neither model system produces an amino acids suite that is completely comparable to that found in the Murchison meteorite. PMID:7277509

Cronin, J R; Gandy, W E; Pizzarello, S

1981-01-01

267

Time-resolved transcriptome analysis of Bacillus subtilis responding to valine, glutamate, and glutamine.  

PubMed

Microorganisms can restructure their transcriptional output to adapt to environmental conditions by sensing endogenous metabolite pools. In this paper, an Agilent customized microarray representing 4,106 genes was used to study temporal transcript profiles of Bacillus subtilis in response to valine, glutamate and glutamine pulses over 24 h. A total of 673, 835, and 1135 amino-acid-regulated genes were identified having significantly changed expression at one or more time points in response to valine, glutamate, and glutamine, respectively, including genes involved in cell wall, cellular import, metabolism of amino-acids and nucleotides, transcriptional regulation, flagellar motility, chemotaxis, phage proteins, sporulation, and many genes of unknown function. Different amino acid treatments were compared in terms of both the global temporal profiles and the 5-minute quick regulations, and between-experiment differential genes were identified. The highlighted genes were analyzed based on diverse sources of gene functions using a variety of computational tools, including T-profiler analysis, and hierarchical clustering. The results revealed the common and distinct modes of action of these three amino acids, and should help to elucidate the specific signaling mechanism of each amino acid as an effector. PMID:19763274

Ye, Bang-Ce; Zhang, Yan; Yu, Hui; Yu, Wen-Bang; Liu, Bao-Hong; Yin, Bin-Cheng; Yin, Chun-Yun; Li, Yuan-Yuan; Chu, Ju; Zhang, Si-Liang

2009-01-01

268

Nonconventional techniques for separation of biosynthetic amino acids.  

PubMed

Amino acids can be obtained by biosynthesis, by protein hydrolysis or by extraction from natural sources. The most efficient methods are the first two, but the separation of amino acids from fermentation broths or protein hydrolysates is rather difficult. Amino acids dissociate in aqueous solutions, forming characteristic ionic species depending on the solution pH-value. These properties make amino acids to be hydrophilic at any pH-value. This paper presents a review of the separation studies of some amino acids by nonconventional methods, namely individual or selective reactive extraction. Separation of some amino acids from their mixture obtained either by fermentation or protein hydrolysis by reactive extraction with different extractants indicated the possibility of the amino acids selective separation as a function of the pH-value of aqueous solution correlated with the acidic or basic character of each amino acid. PMID:24741809

Kloetzer, Lenu?a; Po?taru, M?d?lina; Cheptea, Corina; Ca?caval, D; Galaction, Anca-Irina

2014-01-01

269

Amino acid catabolic pathways of lactic acid bacteria.  

PubMed

Lactic acid bacteria (LAB) constitute a diverse group of Gram positive obligately fermentative microorganisms which include both beneficial and pathogenic strains. LAB generally have complex nutritional requirements and therefore they are usually associated with nutrient-rich environments such as animal bodies, plants and foodstuffs. Amino acids represent an important resource for LAB and their utilization serves a number of physiological roles such as intracellular pH control, generation of metabolic energy or redox power, and resistance to stress. As a consequence, the regulation of amino acid catabolism involves a wide set of both general and specific regulators and shows significant differences among LAB. Moreover, due to their fermentative metabolism, LAB amino acid catabolic pathways in some cases differ significantly from those described in best studied prokaryotic model organisms such as Escherichia coli or Bacillus subtilis. Thus, LAB amino acid catabolism constitutes an interesting case for the study of metabolic pathways. Furthermore, LAB are involved in the production of a great variety of fermented products so that the products of amino acid catabolism are also relevant for the safety and the quality of fermented products. PMID:16893752

Fernández, María; Zúñiga, Manuel

2006-01-01

270

Hypothalamic signaling in anorexia induced by indispensable amino acid deficiency.  

PubMed

Animals exhibit a rapid and sustained anorexia when fed a diet that is deficient in a single indispensable amino acid (IAA). The chemosensor for IAA deficiency resides within the anterior piriform cortex (APC). Although the cellular and molecular mechanisms by which the APC detects IAA deficiency are well established, the efferent neural pathways that reduce feeding in response to an IAA-deficient diet remain to be fully characterized. In the present work, we investigated whether 1) central melanocortin signaling is involved in IAA deficiency-induced anorexia (IAADA) and 2) IAADA engages other key appetite-regulating neuronal populations in the hypothalamus. Rats and mice that consumed a valine-deficient diet (VDD) for 2-3 wk exhibited marked reductions in food intake, body weight, fat and lean body mass, body temperature, and white adipose tissue leptin gene expression, as well as a paradoxical increase in brown adipose tissue uncoupling protein-1 mRNA. Animals consuming the VDD had altered hypothalamic gene expression, typical of starvation. Pharmacological and genetic blockade of central melanocortin signaling failed to increase long-term food intake in this model. Chronic IAA deficiency was associated with a marked upregulation of corticotropin-releasing hormone expression in the lateral hypothalamus, particularly in the parasubthalamic nucleus, an area heavily innervated by efferent projections from the APC. Our observations indicate that the hypothalamic melanocortin system plays a minor role in acute, but not chronic, IAADA and suggest that the restraint on feeding is analogous to that observed after chronic dehydration. PMID:23047987

Zhu, Xinxia; Krasnow, Stephanie M; Roth-Carter, Quinn R; Levasseur, Peter R; Braun, Theodore P; Grossberg, Aaron J; Marks, Daniel L

2012-12-15

271

Peptidases and amino acid catabolism in lactic acid bacteria  

Microsoft Academic Search

The conversion of peptides to free amino acids and their subsequent utilization is a central metabolic activity in prokaryotes. At least 16 peptidases from lactic acid bacteria (LAB) have been characterized biochemically and\\/or genetically. Among LAB, the peptidase systems of Lactobacillus helveticus and Lactococcus lactis have been examined in greatest detail. While there are homologous enzymes common to both systems,

Jeffrey E. Christensen; Edward G. Dudley; Jeffrey A. Pederson; James L. Steele

1999-01-01

272

FgIlv5 is required for branched-chain amino acid biosynthesis and full virulence in Fusarium graminearum.  

PubMed

In this study, we characterized FgIlv5, a homologue of the Saccharomyces cerevisiae keto-acid reductoisomerase (KARI) from the important wheat head scab fungus Fusarium graminearum. KARI is a key enzyme in the branched-chain amino acid (BCAA, including leucine, isoleucine and valine) biosynthetic pathway that exists in a variety of organisms from bacteria to fungi and higher plants, but not in mammals. The FgILV5 deletion mutant ?FgIlv5-4 failed to grow when the culture medium was nutritionally limited for BCAAs. When grown on potato-dextrose agar plates, ?FgIlv5-4 exhibited a significant decrease in aerial hyphae formation and red pigmentation. Conidia formation was also blocked in ?FgIlv5-4. Exogenous addition of 1 mM isoleucine and valine was able to rescue the defects of mycelial growth and conidial morphogenesis. Cellular stress assays showed that ?FgIlv5-4 was more sensitive to osmotic and oxidative stresses than the wild-type strain. In addition, virulence of ?FgIlv5-4 was dramatically reduced on wheat heads, and a low level of deoxynivalenol production was detected in ?FgIlv5-4 in wheat kernels. The results of this study indicate that FgIlv5 is involved in valine and isoleucine biosynthesis and is required for full virulence in F. graminearum. PMID:24493249

Liu, Xin; Wang, Jian; Xu, Jianhong; Shi, Jianrong

2014-04-01

273

Valproate disturbs the balance between branched and aromatic amino acids in rats.  

PubMed

We investigated the effect of valproate (ip, 500 mg/kg), which is regarded as a potent plasma protein tryptophan (TRP) displacer, on the central nervous system (hippocampal) and peripheral (plasma) levels of the aromatic amino acids (AAAs; e.g. TRP, tyrosine and phenylalanine) and branched-chain amino acids (BCAAs; e.g. valine, isoleucine and leucine) as well as the other amino acids (glutamate, GABA, alanine, glutamine, glycine, aspartate and taurine) involved in the regulation of neurotransmission. Furthermore, we investigated whether the changes in the BCAA/AAA ratio affected the hippocampal concentration of monoamines [serotonin (5-HT), dopamine (DA) and noradrenaline (NA)]. Valproic acid (VPA) administration potently modified the balance between the BCAA and AAA. In the brain, the significantly increased AAA and decreased BCAA concentrations were followed by a decrease in the BCAA/AAA ratio. In the plasma, VPA significantly decreased the BCAA and AAA levels. The changes in the BCAA and AAA levels were accompanied by an increase in the NA, DA and 5-HT levels as well as hippocampal 5-HT metabolism. This novel finding indicates that VPA, through the displacement of TRP from its protein-binding sites, could disturb the BCAA/AAA ratio, with central nervous system consequences, including the possible contribution to VPAs effects in affective disorders. PMID:24249529

Maciejak, Piotr; Szyndler, Janusz; Ko?osowska, Karolina; Turzy?ska, Danuta; Sobolewska, Alicja; Walkowiak, Jerzy; P?a?nik, Adam

2014-05-01

274

40 CFR 721.10126 - Alkyl amino substituted triazine amino substituted benezenesulfonic acid reaction product with...  

Code of Federal Regulations, 2010 CFR

...substituted triazine amino substituted benezenesulfonic acid reaction product with naphthalenesulfonato azo substituted phenyl azo substituted benzenesulfonic acid copper compound (generic). 721.10126 Section 721.10126 Protection...

2010-07-01

275

The Use of Amino Acid Linkers in the Conjugation of Paclitaxel with Hyaluronic Acid as Drug Delivery System: Synthesis, Self-Assembled Property, Drug Release, and In Vitro Efficiency  

Microsoft Academic Search

Purpose  A cell-targeted prodrug with good self-assembly properties in aqueous solution was prepared for the anti-cancer drug paclitaxel,\\u000a offering great potential for further investigation.\\u000a \\u000a \\u000a \\u000a Methods  We synthesized hyaluronic acid (HA) with a specific targeting property as a carrier to conjugate with paclitaxel by inserting\\u000a different amino acids as spacers, including valine, leucine, and phenylalanine, respectively. The structure of HA-amino acid-paclitaxel\\u000a conjugates was

Dingcheng Xin; Ying Wang; Jiannan Xiang

2010-01-01

276

Sodium ion-dependent amino acid transport in membrane vesicles of Bacillus stearothermophilus.  

PubMed Central

Amino acid transport in membrane vesicles of Bacillus stearothermophilus was studied. A relatively high concentration of sodium ions is needed for uptake of L-alanine (Kt = 1.0 mM) and L-leucine (Kt = 0.4 mM). In contrast, the Na(+)-H(+)-L-glutamate transport system has a high affinity for sodium ions (Kt less than 5.5 microM). Lithium ions, but no other cations tested, can replace sodium ions in neutral amino acid transport. The stimulatory effect of monensin on the steady-state accumulation level of these amino acids and the absence of transport in the presence of nonactin indicate that these amino acids are translocated by a Na+ symport mechanism. This is confirmed by the observation that an artificial delta psi and delta mu Na+/F but not a delta pH can act as a driving force for uptake. The transport system for L-alanine is rather specific. L-Serine, but not L-glycine or other amino acids tested, was found to be a competitive inhibitor of L-alanine uptake. On the other hand, the transport carrier for L-leucine also translocates the amino acids L-isoleucine and L-valine. The initial rates of L-glutamate and L-alanine uptake are strongly dependent on the medium pH. The uptake rates of both amino acids are highest at low external pH (5.5 to 6.0) and decline with increasing pH. The pH allosterically affects the L-glutamate and L-alanine transport systems. The maximal rate of L-glutamate uptake (Vmax) is independent of the external pH between pH 5.5 and 8.5, whereas the affinity constant (Kt) increases with increasing pH. A specific transport system for the basic amino acids L-lysine and L-arginine in the membrane vesicles has also been observed. Transport of these amino acids occurs most likely by a uniport mechanism.

Heyne, R I; de Vrij, W; Crielaard, W; Konings, W N

1991-01-01

277

A genetically encoded fluorescent amino acid  

PubMed Central

The ability to introduce fluorophores selectively into proteins provides a powerful tool to study protein structure, dynamics, localization, and biomolecular interactions both in vitro and in vivo. Here, we report a strategy for the selective and efficient biosynthetic incorporation of a low-molecular-weight fluorophore into proteins at defined sites. The fluorescent amino acid 2-amino-3-(5-(dimethylamino)naphthalene-1-sulfonamide)propanoic acid (dansylalanine) was genetically encoded in Saccharomyces cerevisiae by using an amber nonsense codon and corresponding orthogonal tRNA/aminoacyl-tRNA synthetase pair. This environmentally sensitive fluorophore was selectively introduced into human superoxide dismutase and used to monitor unfolding of the protein in the presence of guanidinium chloride. The strategy described here should be applicable to a number of different fluorophores in both prokaryotic and eukaryotic organisms, and it should facilitate both biochemical and cellular studies of protein structure and function.

Summerer, Daniel; Chen, Shuo; Wu, Ning; Deiters, Alexander; Chin, Jason W.; Schultz, Peter G.

2006-01-01

278

Allied Health Chemistry Laboratory: Amino Acids, Insulin, Proteins, and Skin  

ERIC Educational Resources Information Center

Presents a laboratory experiment specifically designed for allied health students. The students construct molecular models of amino acids, extract amino acids from their skin with hot water, and chromatographically analyze the skin extract and hydrolyzed insulin. (MLH)

Dever, David F.

1975-01-01

279

Amino Acid Composition of Crystalline Botulinum Toxin, Type A.  

National Technical Information Service (NTIS)

The amino acid composition of botulinum toxin, type A, was determined with the aid of the automatic amino acid analyzer. The results are compared with an earlier largely microbiological analysis. (Author)

D. Stefanye

1965-01-01

280

Amino Acids in Nectar Enhance Longevity of Female Culex quinquefasciatus.  

National Technical Information Service (NTIS)

Culex mosquitoes feed on a wide range of nectars consisting of mostly carbohydrates and amino acids however, little is known about the utilization and effects of these different carbohydrates and their accompanying amino acids on longevity. Culex quinquef...

D. A. Hahn E. M. Vrzal S. A. Allan

2010-01-01

281

Single amino acid supplementation in aminoacidopathies: a systematic review  

PubMed Central

Aminoacidopathies are a group of rare and diverse disorders, caused by the deficiency of an enzyme or transporter involved in amino acid metabolism. For most aminoacidopathies, dietary management is the mainstay of treatment. Such treatment includes severe natural protein restriction, combined with protein substitution with all amino acids except the amino acids prior to the metabolic block and enriched with the amino acid that has become essential by the enzymatic defect. For some aminoacidopathies, supplementation of one or two amino acids, that have not become essential by the enzymatic defect, has been suggested. This so-called single amino acid supplementation can serve different treatment objectives, but evidence is limited. The aim of the present article is to provide a systematic review on the reasons for applications of single amino acid supplementation in aminoacidopathies treated with natural protein restriction and synthetic amino acid mixtures.

2014-01-01

282

Amino acids: metabolism, functions, and nutrition  

Microsoft Academic Search

Recent years have witnessed the discovery that amino acids (AA) are not only cell signaling molecules but are also regulators\\u000a of gene expression and the protein phosphorylation cascade. Additionally, AA are key precursors for syntheses of hormones\\u000a and low-molecular weight nitrogenous substances with each having enormous biological importance. Physiological concentrations\\u000a of AA and their metabolites (e.g., nitric oxide, polyamines, glutathione,

Guoyao Wu

2009-01-01

283

Structure and Function of Cationic Amino Acid Transporters (CATs)  

Microsoft Academic Search

The CAT proteins (CAT for cationic amino acid transporter) are amongst the first mammalian amino acid transporters identified\\u000a on the molecular level and seem to be the major entry path for cationic amino acids in most cells. However, CAT proteins mediate\\u000a also efflux of their substrates and thus may also deplete cells from cationic amino acids under certain circumstances. The

E. I. Closs; J.-P. Boissel; A. Habermeier; A. Rotmann

2006-01-01

284

Amino acids interference on the quantification of reducing sugars by the 3,5-dinitrosalicylic acid assay mislead carbohydrase activity measurements.  

PubMed

This study evaluated the interference of the amino acids tryptophan, cysteine, histidine, tyrosine, hydroxyproline, leucine, proline, serine, glycine, valine, glutamic acid, phenylalanine, and methionine on the measurement of reducing sugars using a phenol-free 3,5-dinitrosalicylic acid (DNS) reagent. It was found that in reaction mixtures containing 20mM of either tryptophan, cysteine, histidine, tyrosine, or hydroxyproline the measurement of 3.7 mM glucose was overestimated by 76%, 50%, 35%, 18%, and 10%, respectively. The amino acids valine, glutamic acid, and phenylalanine did not affect the DNS reaction, while methionine decreased the color development by 5%. The measurement of glucose, xylose, arabinose, and cellobiose at the 3.7-12.4 mM range in the presence of 20 mM cysteine resulted in an overestimated concentration of 34.8-50%. Enzymatic assays for measuring xylanolytic and filter paper activity (FPAse) were conducted in the presence of 20-60 mM cysteine, and compared to cysteine-free assays. In the presence of cysteine, the measured xylanase activity increased threefold and the FPAse activity increased twofold due to the overestimation of the reducing sugar concentrations in the assays. The interference from cysteine was reduced to a maximum of 8.6% when a DNS reagent containing phenol was used. PMID:23103512

Teixeira, Ricardo Sposina Sobral; da Silva, Ayla Sant'Ana; Ferreira-Leitão, Viridiana Santana; da Silva Bon, Elba Pinto

2012-12-01

285

Adult bile acid amino transferase deficiency  

PubMed Central

Patient: Female, 70 Final Diagnosis: Bile acid amino transferase deficiency Symptoms: Headache • indigestion • itching skin • nausea • vomiting Medication: — Clinical Procedure: — Specialty: Gastroenterology and Hepatology Objective: Challenging differential diagnosis Background: Bile acid synthesis impairments are difficult to diagnose due to non-specific manifestations related to progressive failure to absorb essential fatty acids and fat soluble vitamins and failure to maintain normal intestinal microbiota. Case Report: A 70-year-old female presented with long-standing history of recurrent headaches, indigestion, dry, scaly, itching skin, and fluid around knee joints. Quantitative Electroencephalography (QEEG) revealed widespread excess theta maximum in the temporal regions. A rare pattern of elevated plasma glycine and taurine led to suspicion of BAATD. A stool profile employing molecular probes for commensal bacteria revealed elevation of Fusobacteria spp. Implementation of bile acid replacement therapy (BART) produced rapid remission of headache and other symptoms and a three-month follow up stool profile revealed normalization of fecal Fusobacteria populations that remained normal after one year of BART. QEEG analyses 4 weeks following BART showed evidence of significant improvement in CNS functioning. Conclusions: This case illustrates the potential for diagnosis of latent, adult BAATD by finding a unique pattern of plasma amino acids and monitoring of therapy by observing normalization of fecal commensal bacteria and functional brain assessments.

Lord, Richard S.; Tuttle, Daniel M.; Cantor, David S.

2014-01-01

286

Design and Characterization of Auxotrophy-Based Amino Acid Biosensors  

Microsoft Academic Search

Efficient and inexpensive methods are required for the high-throughput quantification of amino acids in physiological fluids or microbial cell cultures. Here we develop an array of Escherichia coli biosensors to sensitively quantify eleven different amino acids. By using online databases, genes involved in amino acid biosynthesis were identified that – upon deletion – should render the corresponding mutant auxotrophic for

Felix Bertels; Holger Merker; Christian Kost

2012-01-01

287

New insights into amino acid metabolism, ?-cell function and diabetes  

Microsoft Academic Search

Specific amino acids are now known to acutely and chronically regulate insulin secretion from pancreatic ?-cellsinvivo andinvitro. Understanding the molecular mechanisms by which amino acids regulate insulin secretion may identify novel targets for future diabetes therapies. Mitochondrial metabolism is crucial for the coupling of amino acid and glucose recognition to the exocytosis of the insulin granules. This is illustrated by

Philip NEWSHOLME; Lorraine BRENNAN; Blanca RUBI; Pierre MAECHLER

2005-01-01

288

Amino acids and osmolarity in honeybee drone haemolymph  

Microsoft Academic Search

Summary In the haemolymph of honeybee drones, concentrations of free amino acids were higher than in worker haemolymph, with different relative proportions of individual amino acids. The overall concentration of free amino acids reached its highest level at the 5th day after adult drone emergence, and after the 9th day only minor changes in the concentration and distribution of free

B. Leonhard; K. Crailsheim

1999-01-01

289

Amino acid and carnitine supplementation in haemodialysed children  

Microsoft Academic Search

Plasma carnitine, amino acids and lipids levels were studied in ten uraemic children treated with haemodialysis and given amino acid supplementation with and without carnitine. As carnitine is synthesised from lysine and methionine and has a significant influence on lipid metabolism, the relationship between these was examined. Amino acid supplementation (0.25 g\\/kg body weight) was started with the intention of

J. Zachwieja; M. Duran; J. A. Joles; P. J. Allers; D. Hurk; J. J. Frankhuisen; R. A. M. G. Donckerwolcke

1994-01-01

290

Amino Acids in Gut Contents During Digestion in the Dog  

Microsoft Academic Search

Analyses of alimentary tract contents for free amino acids demonstrated that various test meals yielded similar amino acid mixtures in the small intestine (Nas- set et al., '55). Gastric and duodenal con tents arising from a test meal protein of unusual amino acid composition, such as zein, were usually identifiable. Jejunal and ileal contents could not be characterized in this

E. S. NASSET

291

Analysis of free amino acids in green coffee beans  

Microsoft Academic Search

To investigate amino acid changes in green coffee beans in the post-harvest period, amino acid concentrations were determined in green beans and after modelled drying, fermentation and storage. After the drying at alternating temperatures up to maximally 40°C, considerable changes in the concentrations of individual amino acids were identified. At the beginning of the storage period, significant changes in concentration

Ulrike Arnold; Eberhard Ludwig

1996-01-01

292

Bioavailable amino acids in sediments: A biomimetic, kinetics based approach  

Microsoft Academic Search

We developed a biomimetic approach, based on direct incubation with proteolytic enzymes, to measure bioavailable amino acids in sediments. The kinetics of release of monomers and oligopeptides, which are amenable to absorption by cells, is measured as either individual or total amino acids. Microbial proteases incubated with fresh sediments yield amino acids at a similar rate as gut juices from

LAWRENCE M. MAYER; LINDA L. SCHICK; THOMAS SAWYER; CRAIG J. PLANTE; PETER A. JUMARS; ROBERT L. SELF

1995-01-01

293

HPLC determination of acidic D-amino acids and their N-methyl derivatives in biological tissues.  

PubMed

D-Aspartate (D-Asp) and N-methyl-D-aspartate (NMDA) occur in the neuroendocrine systems of vertebrates and invertebrates, where they play a role in hormone release and synthesis, neurotransmission, and memory and learning. N-methyl-d-glutamate (NMDG) has also been detected in marine bivalves. Several methods have been used to detect these amino acids, but they require pretreatment of tissue samples with o-phthaldialdehyde (OPA) to remove primary amino acids that interfere with the detection of NMDA and NMDG. We report here a one-step derivatization procedure with the chiral reagent N-alpha-(5-fluoro-2,4-dinitrophenyl)-(D or L)-valine amide, FDNP-Val-NH2, a close analog of Marfey's reagent but with better resolution and higher molar absorptivity. The diastereomers formed were separated by HPLC on an ODS-Hypersil column eluted with TFA/water-TFA/MeCN. UV absorption at 340 nm permitted detection levels as low as 5-10 pmol. D-Asp, NMDA and NMDG peaks were not obscured by other primary or secondary amino acids; hence pretreatment of tissues with OPA was not required. This method is highly reliable and fast (less than 40 min HPLC run). Using this method, we detected D-Asp, NMDA and NMDG in several biological tissues (octopus brain, optical lobe and bucchal mass; foot and mantle of the mollusk Scapharca broughtonii), confirming the results of other researchers. PMID:19277955

Tsesarskaia, Mara; Galindo, Erika; Szókán, Gyula; Fisher, George

2009-06-01

294

Synthesis and characterization of new polyamides derived from alanine and valine derivatives  

PubMed Central

Background Many efforts have been recently devoted to design, investigate and synthesize biocompatible, biodegradable polymers for applications in medicine for either the fabrication of biodegradable devices or as drug delivery systems. Many of them consist of condensation of polymers having incorporated peptide linkages susceptible to enzymatic cleavage. Polyamides (PAs) containing ?-amino acid residues such as L-leucine, L-alanine and L-phenylalanine have been reported as biodegradable materials. Furthermore, polyamides (PAs) derived from C10 and C14 dicarboxylic acids and amide-diamines derived from 1,6-hexanediamine or 1,12-dodecanediamine and L-phenylalanine, L-valyl-L-phenylalanine or L-phenylalanyl-L-valine residues have been reported as biocompatible polymers. We have previously described the synthesis and thermal properties of a new type of polyamides-containing amino acids based on eight new symmetric meta-oriented protected diamines derived from coupling of amino acids namely; Fomc-glycine, Fmoc-alanine, Fomc-valine and Fomc-leucine with m-phenylene diamine or 2,6-diaminopyridine. Results revealed that incorporation of pyridine onto the polymeric backbone of all series decreases the thermal stability. Here we describe another family of polyamides based on benzene dicarboxylic acid, pyridine dicarboxylic acid, and ?-amino acid linked to benzidine and 4,4?-oxydianiline to study the effect of the dicarboxylic acid as well as the amino acids on the nature and thermal stability of the polymers. Results We report here the preparation of a new type of polyamides based on benzene dicarboxylic acid, pyridine dicarboxylic acid, and ?-amino acid linked to benzidine and 4,4?-oxydianiline to study the effect of the dicarboxylic acid as well as the amino acids on the nature and thermal stability of polymers. The thermal properties of the polymers were evaluated by different techniques. Results revealed that structure-thermal property correlation based on changing the dicarboxylic acid monomer or the diamine monomer demonstrated an interesting connection between a single change (changing the dicarboxylic acids in each series while the diamine is fixed) and thermal properties. The newly prepared polymers may possess biodegradability and thus may find some applications as novel biomaterials. Conclusions The thermal properties of the new type of polyamides based on benzene dicarboxylic acid, pyridine dicarboxylic acid, and ?-amino acid (alanine and valine) linked to benzidine and 4,4?-oxydianiline were evaluated by thermal gravimetric (TG), differential thermal gravimetric (DTG) and differential thermal analysis (DTA) techniques. Results revealed that the structure-thermal property correlation based on changing the dicarboxylic acid monomer or the diamine monomer demonstrated an interesting connection between a single change (changing the dicarboxylic acids in each series while the diamine is fixed) and thermal properties. In addition, pyridine-containing polymers exhibited semicrystalline characteristic with melting temperature, Tm. where none of the valine-containing polymers showed a melting and crystallization peak indicating that the polymers were amorphous. This is expected since L-valine side chain can inhibit close packing and eliminate crystallization. The newly prepared polymers may possess biodegradability and thus may find some applications as novel biomaterials.

2012-01-01

295

Variation of the amino acid content of Arabidopsis seeds by expressing soybean aspartate aminotransferase gene.  

PubMed

We have increased the contents of several amino acids in the seeds of Arabidopsis thaliana by introduction of aspartate aminotransferase (AAT), an enzyme of the aspartate biosynthetic pathway. mRNA was prepared from one-week-old seedlings of Glycine max cv. enrei and the cDNA encoding AAT5 was isolated and linked to the CaMV35S promoter in the plant vector pBI121. The AAT5 gene encodes a protein of 462 amino acid residues that shows 51% amino acid sequence similarity to A. thaliana chloroplast Asp3. The soybean AAT5 also contains a chloroplast transit peptide and is able to functionally complement a Saccharomyces cerevisiae mutant lacking the Asp5 gene. A. thaliana was transformed with the AAT5 gene from Agrobacterium tumefaciens by the vacuum infiltration method. The AAT5 gene was detected in the transcript and genomic DNA from the transgenic T2 plants. The T3 progeny showed a 3:1 segregation ratio indicating the presence of a single integration. Expression of G. max AAT5 in A. thaliana transformants caused 3-, 4-, 23-, and 50-fold increases in the contents of free glycine, alanine, asparagine, and glutamine, respectively, in the T3 seeds. A decrease in the contents of valine, tyrosine, isoleucine, leucine, and phenylalanine by several folds was also observed. Thus, it is of interest that a key gene expression resulted in marked changes of metabolites in plant seeds. PMID:16233295

Murooka, Yoshikatsu; Mori, Yukiko; Hayashi, Makoto

2002-01-01

296

Precise measurement for the purity of amino acid and peptide using quantitative nuclear magnetic resonance.  

PubMed

Precise measurement for the purity of organic compounds will fundamentally improve the capabilities and measurement services of the organic chemical analysis. Quantitative nuclear magnetic resonance (qNMR) is an important method to assess the purity of organic compounds. We presented a precise measurement method for the purity of small molecule with identification of impurities. In addition, the qNMR was rarely applied to purity of large compounds such as peptide, for which qNMR peaks are too crowded. Other than general idea of qNMR, we removed unwanted exchangeable peaks by proton exchange, as a new approach for qNMR, to make the quantitative protons of peptide isolated, which can ensure precise measurement. Moreover, a suitable internal standard, acesulfame potassium, was applied. The analytes were valine and peptide T5, due to their importance for protein analysis. For valine, the intraday CV was 0.052%, and the interday CV during 8 months was 0.071%. For peptide T5, simpler operation, shorter analytical time (1h vs. 3 days) and smaller CV (0.36% vs. 0.93%) were achieved by qNMR, compared with a traditional method (amino acid based isotope labeled mass spectrometry) via a hydrolysis reaction. This method has greatly increased the quantitative precision of qNMR for small compounds, and extended application scope of qNMR from small compounds to peptides. PMID:24840420

Huang, Ting; Zhang, Wei; Dai, Xinhua; Zhang, Xiaoguang; Quan, Can; Li, Hongmei; Yang, Yi

2014-07-01

297

Facile fabrication of superhydrophobic flower-like polyaniline architectures by using valine as a dopant in polymerization  

NASA Astrophysics Data System (ADS)

A facile method was developed to fabricate superhydrophobic, flower-like polyanline (PANI) architectures with hierarchical nanostructures by adding valine in polymerization as a dopant. The water contact angle of the prepared PANI film was measured to be 155.3°, and the hydrophobic surface of the PANI architectures can be tuned easily by varying the polymerization time as well as valine doping quantity. It is believed that valine plays an important role in not only growth of the hierarchical PANI structures but also formation of the superhydrophobic surface, for it provides functional groups such as sbnd COOH, sbnd NH2 and a hydrophobic terminal group which may further increase intra-/inter-molecular interactions including hydrogen bonding, ?-? stacking and hydrophobic properties. Similar flower-like PANI architectures have been prepared successfully by employing other amino acids such as threonine, proline and arginine. This method makes it possible for widespread applications of superhydrophobic PANI film due to its simplicity and practicability.

Sun, Jun; Bi, Hong

2012-03-01

298

Specificity of amino acid regulated gene expression: analysis of genes subjected to either complete or single amino acid deprivation  

Microsoft Academic Search

Amino acid deprivation activates the amino acid response (AAR) pathway that enhances transcription of genes containing an\\u000a amino acid response element (AARE). The present data reveal a quantitative difference in the response to deprivation of individual\\u000a amino acids. The AAR leads to increased eukaryotic initiation factor 2? (eIF2?) phosphorylation and ATF4 translation. When\\u000a HepG2 cells were deprived of an individual

S. S. Palii; C. E. Kays; C. Deval; A. Bruhat; P. Fafournoux; M. S. Kilberg

2009-01-01

299

Computational model of abiogenic amino acid condensation to obtain a polar amino acid profile.  

PubMed

In accordance with the second law of thermodynamics, the Universe as a whole tends to higher entropy. However, the sequence of far-from-equilibrium events that led to the emergence of life on Earth could have imposed order and complexity during the course of chemical reactions in the so-called primordial soup of life. Hence, we may expect to find characteristic profiles or biases in the prebiotic product mixtures, as for instance among the first amino acids. Seeking to shed light on this hypothesis, we have designed a high performance computer program that simulates the spontaneous formation of the amino acid monomers in closed environments. The program was designed in reference to a prebiotic scenario proposed by Sydney W. Fox. The amino acid abundances and their polarities as the two principal biases were also taken into consideration. We regarded the computational model as exhaustive since 200 000 amino acid dimers were formed by simulation, subsequently expressed in a vector and compared with the corresponding amino acid dimers that were experimentally obtained by Fox. We found a very high similarity between the experimental results and our simulations. PMID:24809066

Polanco, Carlos; Buhse, Thomas; Samaniego, José Lino; Castañón González, Jorge Alberto; Estrada, Miguel Arias

2014-01-01

300

Hair and amino acids: the interactions and the effects.  

PubMed

The interaction and the function of some amino acids in hair care applications are discussed. When amino acids are applied to hair in the form of simple aqueous solution, uptake of the amino acids is mainly controlled by ionic equilibrium. When amino acids were incorporated in a hair conditioner, the result was quite different, suggesting the importance of interaction between the amino acids and the cationic surfactants. Uptake of pyrrolidone carboxylic acid (PCA), a derivative of glutamic acid, is enhanced by combining with arginine, an amino with strong affinity towards hair. Effects of some amino acids on bleached/dyed hair are described. A hair conditioner incorporated with alanine improves hair surface hydrophobicity of bleach-damaged hair. Histidine and phenylalanine improve tensile strength. PCA was proved to be effective to improve color-retention of dyed hair. PMID:17728935

Oshimura, Eiko; Abe, Hiroshi; Oota, Rina

2007-01-01

301

Synthesis of N-kojic-amino acid and N-kojic-amino acid-kojiate and their tyrosinase inhibitory activity  

Microsoft Academic Search

Ten amino acid derivatives of kojic acid were synthesized to improve the tyrosinase inhibitory activity of kojic acid. Almost all derivatives showed stronger activities than kojic acid, and in general, N-kojic-amino acid-kojiate was found to have a higher inhibitory potency than N-kojic-amino acid. Among them, the N-kojic-L-phenylalanyl kojiate was the strongest inhibitor and its IC50 value was 1\\/380 that for

Yoshikane Kobayashi; Hiroshi Kayahara; Koji Tadasa; Hiroshi Tanaka

1996-01-01

302

Competitive Inhibition of Amino Acid Uptake Suppresses Chlamydial Growth: Involvement of the Chlamydial Amino Acid Transporter BrnQ  

Microsoft Academic Search

Chlamydiaceae are obligate intracellular bacterial pathogens that strictly depend on host metabolites, such as nucleotides, lipids, and amino acids. Depletion of amino acids in cell culture media results in abnormal chlamydial development in vitro. Surprisingly, enrichment of certain amino acids also retards chlamydial growth. Our experiments revealed that the antichlamydial effects are largely independent of changes in the host cell

Peter R. Braun; Hesham Al-Younes; Joscha Gussmann; Jeannette Klein; Erwin Schneider; Thomas F. Meyer

2008-01-01

303

?-Transaminase-catalyzed asymmetric synthesis of unnatural amino acids using isopropylamine as an amino donor.  

PubMed

Isopropylamine is an ideal amino donor for reductive amination of carbonyl compounds by ?-transaminase (?-TA) owing to its cheapness and high volatility of a ketone product. Here we developed asymmetric synthesis of unnatural amino acids via ?-TA-catalyzed amino group transfer between ?-keto acids and isopropylamine. PMID:23897436

Park, Eul-Soo; Dong, Joo-Young; Shin, Jong-Shik

2013-09-25

304

Amino-Terminal Amino Acid Sequence of the Silkworm Prothoracicotropic Hormone: Homology with Insulin  

Microsoft Academic Search

Three molecular forms of prothoracicotropic hormone were isolated from the head of the adult silkworm, Bombyx mori, and the amino acid sequence of 19 amino acid residues in the amino terminus of these prothoracicotropic hormones was determined. These residues exhibit significant homology with insulin and insulin-like growth factors.

Hiromichi Nagasawa; Hiroshi Kataoka; Akira Isogai; Saburo Tamura; Akinori Suzuki; Hironori Ishizaki; Akira Mizoguchi; Yuko Fujiwara; Atsushi Suzuki

1984-01-01

305

Editing of errors in selection of amino acids for protein synthesis.  

PubMed Central

All living cells must conduct protein synthesis with a high degree of accuracy maintained in the transmission and flow of information from gene to finished protein product. One crucial "quality control" point in maintaining a high level of accuracy is the selectivity by which aminoacyl-tRNA synthetases furnish correctly activated amino acids, attached to tRNA species, as the building blocks for growing protein chains. During selection of amino acids, synthetases very often have to distinguish the cognate substrate from a homolog having just one fewer methyl group in its structure. The binding energy of a methyl group is estimated to contribute only a factor of 100 to the specificity of binding, yet synthetases distinguish such closely related amino acids with a discrimination factor of 10,000 to 100,000. Examples of this include methionine versus homocysteine, isoleucine versus valine, alanine versus glycine, and threonine versus serine. Many investigators have demonstrated in vitro the ability of certain aminoacyl-tRNA synthetases to edit, that is, correct or prevent incorrect attachment of amino acids to tRNA molecules. Several major editing pathways are now established from in vitro data. Further, at least some aminoacyl-tRNA synthetases have recently been shown to carry out the editing function in vivo. Editing has been demonstrated to occur in both Escherichia coli and Saccharomyces cerevisiae. Significant energy is expended by the cell for editing of misactivated amino acids, which can be reflected in the growth rate. Because of this, cellular levels of aminoacyl-tRNA synthetases, as well as amino acid biosynthetic pathways which yield competing substrates for protein synthesis, must be carefully regulated to prevent excessive editing. High-level expression of recombinant proteins imposes a strain on the biosynthetic capacity of the cell which frequently results in misincorporation of abnormal or wrong amino acids owing in part to limited editing by synthetases. Unbalanced amino acid pools associated with some genetic disorders in humans may also lead to errors in tRNA aminoacylation. The availability of X-ray crystallographic structures of some synthetases, combined with site-directed mutagenesis, allows insights into molecular details of the extraordinary selectivity of synthetases, including the editing function.

Jakubowski, H; Goldman, E

1992-01-01

306

Contrasting plasma free amino acid patterns in elite athletes: association with fatigue and infection  

PubMed Central

AIM: There is little information on the plasma free amino acid patterns of elite athletes against which fatigue and nutrition can be considered. Therefore the aim was to include analysis of this pattern in the medical screening of elite athletes during both especially intense and light training periods. METHODS: Plasma amino acid analysis was undertaken in three situations. (1) A medical screening service was offered to elite athletes during an intense training period before the 1992 Olympics. Screening included a blood haematological/biochemical profile and a microbial screen in athletes who presented with infection. The athletes were divided into three groups who differed in training fatigue and were considered separately. Group A (21 track and field athletes) had no lasting fatigue; group B (12 judo competitors) reported heavy fatigue at night but recovered overnight to continue training; group C (18 track and field athletes, one rower) had chronic fatigue and had been unable to train normally for at least several weeks. (2) Athletes from each group were further screened during a post- Olympic light training period. (3) Athletes who still had low amino acid levels during the light training period were reanalysed after three weeks of additional protein intake. RESULTS: (1) The pre-Olympics amino acid patterns were as follows. Group A had a normal amino acid pattern (glutamine 554 (25.2) micromol/l, histidine 79 (6.1) micromol/l, total amino acids 2839 (92.1) micromol/l); all results are means (SEM). By comparison, both groups B and C had decreased plasma glutamine (average 33%; p<0.001) with, especially in group B, decreased histidine, glucogenic, ketogenic, and branched chain amino acids (p<0.05 to p<0.001). None in group A, one in group B, but ten athletes in group C presented with infection: all 11 athletes had plasma glutamine levels of less than 450 micromol/l. No intergroup differences in haematological or other blood biochemical parameters, apart from a lower plasma creatine kinase activity in group C than in group B (p<0.05) and a low neutrophil to lymphocyte ratio in the athletes with viral infections (1.2 (0.17)), were found. (2) During post-Olympic light training, group A showed no significant amino acid changes. In contrast, group B recovered normal amino acid levels (glutamine 528 (41.4) micromol/l, histidine 76 (5.3) micromol/l, and total amino acids 2772 (165) micromol/l) (p<0.05 to p<0.001) to give a pattern comparable with that of group A, whereas, in group C, valine and threonine had increased (p<0.05), but glutamine (441 (24.5) micromol/l) and histidine (58 (5.3) micromol/l) remained low. Thus none in group A, two in group B, but ten (53%) in group C still had plasma glutamine levels below 450 micromol/l, including eight of the 11 athletes who had presented with infection. (3) With the additional protein intake, virtually all persisting low glutamine levels increased to above 500 micromol/l. Plasma glutamine rose to 592 (35.1) micromol/l and histidine to 86 (6.0) micromol/l. Total amino acids increased to 2761 (128) micromol/l (p<0.05 to p<0.001) and the amino acid pattern normalised. Six of the ten athletes on this protein intake returned to increased training within the three weeks. CONCLUSION: Analysis of these results provided contrasting plasma amino acid patterns: (a) a normal pattern in those without lasting fatigue; (b) marked but temporary changes in those with acute fatigue; (c) a persistent decrease in plasma amino acids, mainly glutamine, in those with chronic fatigue and infection, for which an inadequate protein intake appeared to be a factor. ???

Kingsbury, K. J.; Kay, L.; Hjelm, M.

1998-01-01

307

Practical synthesis of fluorous oxazolidinone chiral auxiliaries from alpha-amino acids.  

PubMed

[reaction: see text] A series of new fluorous-supported oxazolidinone chiral auxiliaries has been prepared using a versatile and general five-step pathway, starting from readily available chiral alpha-amino acids. The key feature of this synthesis is the efficient generation of a suitably active perfluoroalkyllithium species. By use of this protocol, the auxiliaries can be obtained in high enantiomeric purity and on multigram scales from L-phenylalanine and L-valine with overall yields as high as 55%. The new methodology also incorporates fluorous solid-phase extraction on the large scale, allowing bulk quantities (up to 25 g) of fluorous compounds to be purified from the crude reaction mixture. PMID:16292825

Hein, Jason E; Geary, Laina M; Jaworski, Ashley A; Hultin, Philip G

2005-11-25

308

New enzymatic method of chiral amino acid synthesis by dynamic kinetic resolution of amino acid amides: use of stereoselective amino acid amidases in the presence of alpha-amino-epsilon-caprolactam racemase.  

PubMed

D- and L-amino acids were produced from L- and D-amino acid amides by D-aminopeptidase from Ochrobactrum anthropi C1-38 and L-amino acid amidase from Pseudomonas azotoformans IAM 1603, respectively, in the presence of alpha-amino-epsilon-caprolactam racemase from Achromobacter obae as the catalyst by dynamic kinetic resolution of amino acid amides. PMID:17586677

Yamaguchi, Shigenori; Komeda, Hidenobu; Asano, Yasuhisa

2007-08-01

309

Organic geochemistry of amino acids: Precambrian to recent  

SciTech Connect

Since the discovery of amino acids in fossils (Abelson, 1954), considerable effort has been made to elucidate the origin and distribution of amino acids in geologic materials. Racemization and decomposition reactions of amino acids and peptides derived via the natural hydrolysis of protein constituents of organisms have been extensively studied. While the ubiquity of amino acids presents a challenge for discerning their indigeneity in geologic samples, careful analyses have resulted in successful applications of amino acid racemization and decomposition reactions for investigations of geochronologic, paleoclimatic, stratigraphic, diagenetic and chemotaxonomic problems for Quaternary age samples. An investigation of amino acids in sediments from Baffin Island fjords indicates that their distribution may also provide data with respect to the relative contributions of marine and terrigenous organic matter to recent sediments. While the absence of unstable amino acids and the presence of racemic amino acids in a sample may preclude very recent contamination, the possibility of retardation of amino acid racemization rates subsequent to geopolymer formation must also be considered. Studies of amino acids in Paleozoic, Mesozoic and early Cenozoic age samples are limited. Precambrian samples, however, have received much attention, given the potential (however slight) for isolating compounds representative of the earliest living systems. A future approach for elucidating the origin(s) of amino acids in ancient samples may be analyses of their individual stable isotopic compositions.

Engel, M.H.; Macko, S.A.

1985-01-01

310

Plasma-free amino acid profiling of cervical cancer and cervical intraepithelial neoplasia patients and its application for early detection.  

PubMed

In this study, plasma-free amino acid profiles were used to investigate pre-cancerous cervical intraepithelial neoplasia (CIN) and cervical squamous cell carcinoma (CSCC) metabolic signatures in plasma. Additionally, the diagnostic potential of these profiles was assessed, as well as their ability to provide novel insight into CSCC metabolism and systemic effects. Plasma samples from CIN patients (n = 26), CSCC patients (n = 22), and a control healthy group (n = 35) were analyzed by high-performance liquid chromatography, and their spectral profiles were subjected to the t test for statistical significance. Potential metabolic biomarkers were identified using database comparisons that examine the significance of metabolites. Compared with healthy controls, patients with CIN and CSCC demonstrated lower levels of plasma amino acids; plasma levels of arginine and threonine were increased in CIN patients but were decreased in cervical cancer patients. Additionally, the levels of a larger group of amino acids (aspartate, glutamate, asparagine, serine, glycine, histidine, taurine, tyrosine, valine, methionine, lysine, isoleucine, leucine, and phenylalanine) were gradually reduced from CIN to invasive cancer. These findings suggest that plasma-free amino acid profiling has great potential for improving cancer screening and diagnosis and for understanding disease pathogenesis. Plasma-free amino acid profiles may have the potential be used to determine cancer diagnoses in the early stage from a single blood sample and may enhance our understanding of its mechanisms. PMID:24068431

Hasim, Ayshamgul; Aili, Aixingzi; Maimaiti, Aminigul; Mamtimin, Batur; Abudula, Abulizi; Upur, Halmurat

2013-10-01

311

Amino Acid Metabolism of Pea Leaves  

PubMed Central

Short term (2-hour) incorporation of nitrogen from nitrate, glutamine, or asparagine was studied by supplying them as unlabeled (14N) tracers to growing pea (Pisum sativum L.) leaves, which were previously labeled with 15N, and then following the elimination of 15N from various amino components of the tissue. Most components had active and inactive pools. Ammonia produced from nitrate was assimilated through the amide group of glutamine. When glutamine was supplied, its nitrogen was rapidly transferred to glutamic acid, asparagine, and other products, and there was some transfer to ammonia. Nitrogen from asparagine was widely distributed into ammonia and amino compounds. There was a rapid direct transfer to glutamine, which did not appear to involve free ammonia. Alanine nitrogen could be derived directly from asparagine, probably by transamination. Homoserine was synthesized in substantial amounts from all three nitrogen sources. Homoserine appears to derive nitrogen more readily from asparagine than from free aspartic acid. A large proportion of the pool of ?-aminobutyric acid turned over, and was replenished with nitrogen from all three supplied sources.

Bauer, Alfred; Joy, Kenneth W.; Urquhart, Aileen A.

1977-01-01

312

Biosynthesis of amino acids in Clostridium pasteurianum  

PubMed Central

1. Clostridium pasteurianum was grown on a synthetic medium with the following carbon sources: (a) 14C-labelled glucose, alone or with unlabelled aspartate or glutamate, or (b) unlabelled glucose plus 14C-labelled aspartate, glutamate, threonine, serine or glycine. The incorporation of 14C into the amino acids of the cell protein was examined. 2. In both series of experiments carbon from exogenous glutamate was incorporated into proline and arginine; carbon from aspartate was incorporated into glutamate, proline, arginine, lysine, methionine, threonine, isoleucine, glycine and serine. Incorporations from the other exogenous amino acids indicated the metabolic sequence: aspartate ? threonine ? glycine ? serine. 3. The following activities were demonstrated in cell-free extracts of the organism: (a) the formation of aspartate by carboxylation of phosphoenolpyruvate or pyruvate, followed by transamination; (b) the individual reactions of the tricarboxylic acid route to 2-oxoglutarate from oxaloacetate; glutamate dehydrogenase was not detected; (c) the conversion of aspartate into threonine via homoserine; (d) the conversion of threonine into glycine by a constitutive threonine aldolase; (e) serine transaminase, phosphoserine transaminase, glycerate dehydrogenase and phosphoglycerate dehydrogenase. This last activity was abnormally high. 4. The combined evidence indicates that in C. pasteurianum the biosynthetic role of aspartate and glutamate is generally similar to that in aerobic and facultatively aerobic organisms, but that glycine is synthesized from glucose via aspartate and threonine.

Dainty, R. H.; Peel, J. L.

1970-01-01

313

Neurochemical study of amino acids in rodent brain structures using an improved gas chromatography-mass spectrometry method.  

PubMed

The analysis of amino acid levels is crucial for neuroscience studies because of the roles of these molecules as neurotransmitters and their influence on behavior. The present study describes the distribution and levels of 16 amino acids (alanine, asparagine, aspartic acid, cysteine, glycine, glutamic acid, isoleucine, leucine, lysine, methionine, phenylalanine, proline, sarcosine, serine, valine, and threonine) in brain tissues (prefrontal cortex, striatum, hippocampus and cerebellum) and the serum. Neurochemical analysis was performed on Wistar rats and C57BL/6 mice using an efficient method for extraction, a fast microwave-assisted derivatization and gas chromatography-mass spectrometry analysis. The amino acid concentration varied across brain regions for 14 of the 16 analyzed molecules, with detection limits ranging from 0.02±0.005?molL(-1) to 7.07±0.05?molL(-1). In rats, the concentrations of alanine, glycine, methionine, serine and threonine were higher in prefrontal cortex than in other areas, whereas in mice, the concentrations of glutamic acid, leucine and proline were highest in the hippocampus. In conclusion, this study provides a cerebral profile of amino acids in brain regions and the serum of rats and mice. PMID:24321291

Pinto, Mauro Cunha Xavier; de Paiva, Maria José Nunes; Oliveira-Lima, Onésia Cristina; Menezes, Helvécio Costa; Cardeal, Zenilda de Lourdes; Gomez, Marcus Vinícius; Resende, Rodrigo Ribeiro; Gomez, Renato Santiago

2014-01-01

314

Review: Taurine: A "very essential" amino acid  

PubMed Central

Taurine is an organic osmolyte involved in cell volume regulation, and provides a substrate for the formation of bile salts. It plays a role in the modulation of intracellular free calcium concentration, and although it is one of the few amino acids not incorporated into proteins, taurine is one of the most abundant amino acids in the brain, retina, muscle tissue, and organs throughout the body. Taurine serves a wide variety of functions in the central nervous system, from development to cytoprotection, and taurine deficiency is associated with cardiomyopathy, renal dysfunction, developmental abnormalities, and severe damage to retinal neurons. All ocular tissues contain taurine, and quantitative analysis of ocular tissue extracts of the rat eye revealed that taurine was the most abundant amino acid in the retina, vitreous, lens, cornea, iris, and ciliary body. In the retina, taurine is critical for photoreceptor development and acts as a cytoprotectant against stress-related neuronal damage and other pathological conditions. Despite its many functional properties, however, the cellular and biochemical mechanisms mediating the actions of taurine are not fully known. Nevertheless, considering its broad distribution, its many cytoprotective attributes, and its functional significance in cell development, nutrition, and survival, taurine is undoubtedly one of the most essential substances in the body. Interestingly, taurine satisfies many of the criteria considered essential for inclusion in the inventory of neurotransmitters, but evidence of a taurine-specific receptor has yet to be identified in the vertebrate nervous system. In this report, we present a broad overview of the functional properties of taurine, some of the consequences of taurine deficiency, and the results of studies in animal models suggesting that taurine may play a therapeutic role in the management of epilepsy and diabetes.

Shen, Wen

2012-01-01

315

Amino acids, precursors for cationic and anionic intercalation synthesis and characterization of amino acid pillared materials  

NASA Astrophysics Data System (ADS)

The preparation and characterization of amino acid pillared materials are reported in this contribution. Host substances were Na-montmorillonite for cationic and hydrotalcite for anionic pillaring. Guest molecules were L-phenylalanine and L-tyrosine. The pillared materials were characterized by powder X-ray diffraction, BET measurements and FT-IR spectroscopy. Pillaring was successful: the layers propped open and the basal distances increased significantly. For hydrotalcite this increase was always significantly larger than for montmorillonite. This fact indicated that the spatial arrangement of the amino acid moieties is widely different. A model for this arrangement is given.

Fudala, Á.; Pálinkó, I.; Kiricsi, I.

1999-05-01

316

Extraterrestrial amino acids in the Almahata Sitta meteorite  

NASA Astrophysics Data System (ADS)

Amino acid analysis of a meteorite fragment of asteroid 2008 TC3 called Almahata Sitta was carried out using reverse-phase liquid chromatography coupled with UV fluorescence detection and time-of-flight mass spectrometry (LC-FD/ToF-MS) as part of a sample analysis consortium. LC-FD/ToF-MS analyses of hot-water extracts from the meteorite revealed a complex distribution of two- to seven-carbon aliphatic amino acids and one- to three-carbon amines with abundances ranging from 0.5 to 149 parts-per-billion (ppb). The enantiomeric ratios of the amino acids alanine, ?-amino-n-butyric acid, 2-amino-2-methylbutanoic acid (isovaline), and 2-aminopentanoic acid (norvaline) in the meteorite were racemic (D/L ˜ 1), indicating that these amino acids are indigenous to the meteorite and not terrestrial contaminants. Several other nonprotein amino acids were also identified in the meteorite above background levels including ?-aminoisobutyric acid (?-AIB), 4-amino-2-methylbutanoic acid, 4-amino-3-methylbutanoic acid, and 3-, 4-, and 5-aminopentanoic acid. The total abundances of isovaline and ?-AIB in Almahata Sitta are approximately 1000 times lower than the abundances of these amino acids found in the CM carbonaceous chondrite Murchison. The extremely low abundances and unusual distribution of five-carbon amino acids in Almahata Sitta compared to CI, CM, and CR carbonaceous chondrites may reflect extensive thermal alteration of amino acids on the parent asteroid by partial melting during formation or subsequent impact shock heating. It is also possible that amino acids were synthesized by catalytic reactions on the parent body after asteroid 2008 TC3 cooled to lower temperatures, or introduced as a contaminant from unrelated meteorite clasts and chemically altered by ?-decarboxylation.

Glavin, Daniel P.; Aubrey, Andrew D.; Callahan, Michael P.; Dworkin, Jason P.; Elsila, Jamie E.; Parker, Eric T.; Bada, Jeffrey L.; Jenniskens, Peter; Shaddad, Muawia H.

2010-10-01

317

Amino Acid Formation on Saturn's Inner Satellites  

NASA Astrophysics Data System (ADS)

Titan's atmosphere contributes nitrogen atoms and ions to the Saturnian magnetosphere. These ions have inward motion towards Saturn and should impact the inner satellites, thereby inducing a complex nitrogen oxides chemistry in the surfaces via their interaction with the water ice present. Species formed may include NO, NO2, NO3, HNO2, HNO3, NH2OH, HNO, NH, NH2, N2O, HNNO, and N2. If the surfaces also include CO2, then other species that may be formed as a result of N+ impact into H2O/CO2 ice will be HNCO, NCO and R-OCN. Successive reaction of HNCO with H and CO (which occur in irradiated H2O/CO2 ice) could lead to the smallest amino acid, glycine, in only 5 steps. Addition of CO to HNCO with successive hydrogenation of the oxygen atoms forms an -OH group with a C=O bond still present. Migration of the OH onto the C=O carbon yields a carboxylic acid group (-COOH). The HNCO -> Glycine conversion utilizes only simple and exothermic addition and rearrangement reactions. Both H and CO would be mobile in the water/CO2 ice crystal at the temperatures on the Saturnian satellites. Every step in the sequence is calculated to be exothermic, and the entire sequence is exothermic by a total of 231 kcal/mole. Therefore these sequences may occur under the temporary non-equilibrium conditions resulting from high-energy particle impact and subsequent residual heating. Glycine has its own radiolysis products, such as CHOCOOH (glyoxylic acid), CH3NH2 (methyl amine), HCHO, NH3, H2O2, and H2. Formation of higher-order amino acids, such as alanine and aminobutyric acids, might also occur, from solid-phase radiolysis or gas-phase ionic synthesis of combinations of some of the smaller molecules in the sequence.

Delitsky, M. L.; Lane, A. L.; Tidwell, T. T.; Henry-Riyad, H.

2002-09-01

318

Valine requirement of nursery pigs.  

PubMed

Six experiments were conducted to determine the true digestible valine requirement of 5- to 20-kg pigs. In Exp. 1, a valine-deficient diet for 5- to 10-kg pigs was developed and validated in terms of growth performance in response to supplemental L-valine. A different basal diet was validated for 10- to 20-kg pigs in Exp. 2. Both diets were demonstrated to be deficient in valine and to support performance equivalent to typical nursery diets when fortified with L-valine. In Exp. 3, true ileal digestibility of valine in the two basal diets was determined in eight pigs fitted with a simple T-cannula at the terminal ileum. Another four pigs received an enzymatically hydrolyzed casein-based diet to determine endogenous contributions to collected ileal digesta. The two diets were found to have true valine digestibilities of 82% (5- to 10-kg pigs) and 86% (10- to 20-kg pigs). In Exp. 4, 80 weaned pigs (5.8 kg) were offered the basal diet fortified with five incremental doses (0.08%) of L-valine. Weight gain increased quadratically (P < 0.05) with increasing levels of valine. Broken-line analysis revealed a true digestible valine requirement of 0.86 +/- 0.03%. In Exp. 5, the true digestible valine requirement of 10- to 20-kg pigs was estimated with 120 pigs (10.9 kg) using the second basal diet fortified with six incremental doses (0.05%) of L-valine. The data suggested a digestible valine requirement level of about 0.775%, which was reevaluated in Exp. 6, wherein pigs did not respond to levels of digestible valine higher than 0.775%. In conclusion, requirement estimates were 2.50 and 2.22 g of true digestible valine per megacalorie of ME for 5- to 10- and 10- to 20-kg pigs, respectively. These empirical estimates are in close agreement with recent estimates of the National Research Council Subcommittee on Swine Nutrition of 2.48 and 2.11 g of true digestible valine per megacalorie of ME, respectively. PMID:11374542

Mavromichalis, I; Kerr, B J; Parr, T M; Albin, D M; Gabert, V M; Baker, D H

2001-05-01

319

Formation of Amino Acid Thioesters for Prebiotic Peptide Synthesis: Catalysis By Amino Acid Products  

NASA Technical Reports Server (NTRS)

The origin of life can be described as a series of events in which a prebiotic chemical process came increasingly under the control of its catalytic products. In our search for this prebiotic process that yielded catalytic takeover products (such as polypeptides), we have been investigating a reaction system that generates peptide-forming amino acid thioesters from formaldehyde, glycolaldehyde, and ammonia in the presence of thiols. As shown below, this model process begins by aldol condensation of formaldehyde and glycolaldehyde to give trioses and releases. These sugars then undergo beta-dehydration yielding their respective alpha-ketoaldehydes. Addition of ammonia to the alpha-ketoaldehydes yields imines which can either: (a) rearrange in the presence of thesis to give amino acid thioesters or (be react with another molecule of aldehyde to give imidazoles. This 'one-pot' reaction system operates under mild aqueous conditions, and like modem amino acid biosynthesis, uses sugar intermediates which are converted to products by energy-yielding redox reactions. Recently, we discovered that amino acids, such as the alanine reaction product, catalyze the first and second steps of the process. In the presence of ammonia the process also generates other synthetically useful products, like the important biochemical -- pyruvic acid.

Weber, Arthur L.; DeVincenzi, Donald L. (Technical Monitor)

1999-01-01

320

Identification, Purification, and Characterization of a Novel Amino Acid Racemase, Isoleucine 2-Epimerase, from Lactobacillus Species  

PubMed Central

Accumulation of d-leucine, d-allo-isoleucine, and d-valine was observed in the growth medium of a lactic acid bacterium, Lactobacillus otakiensis JCM 15040, and the racemase responsible was purified from the cells and identified. The N-terminal amino acid sequence of the purified enzyme was GKLDKASKLI, which is consistent with that of a putative ?-aminobutyrate aminotransferase from Lactobacillus buchneri. The putative ?-aminobutyrate aminotransferase gene from L. buchneri JCM 1115 was expressed in recombinant Escherichia coli and then purified to homogeneity. The enzyme catalyzed the racemization of a broad spectrum of nonpolar amino acids. In particular, it catalyzed at high rates the epimerization of l-isoleucine to d-allo-isoleucine and d-allo-isoleucine to l-isoleucine. In contrast, the enzyme showed no ?-aminobutyrate aminotransferase activity. The relative molecular masses of the subunit and native enzyme were estimated to be about 49 kDa and 200 kDa, respectively, indicating that the enzyme was composed of four subunits of equal molecular masses. The Km and Vmax values of the enzyme for l-isoleucine were 5.00 mM and 153 ?mol·min?1·mg?1, respectively, and those for d-allo-isoleucine were 13.2 mM and 286 ?mol·min?1·mg?1, respectively. Hydroxylamine and other inhibitors of pyridoxal 5?-phosphate-dependent enzymes completely blocked the enzyme activity, indicating the enzyme requires pyridoxal 5?-phosphate as a coenzyme. This is the first evidence of an amino acid racemase that specifically catalyzes racemization of nonpolar amino acids at the C-2 position.

Mutaguchi, Yuta; Ohmori, Taketo; Wakamatsu, Taisuke; Doi, Katsumi

2013-01-01

321

Amino acid transport across the tonoplast of vacuoles isolated from barley mesophyll protoplasts: Uptake of alanine, leucine, and glutamine. [Hordeum vulgare L  

SciTech Connect

Mesophyll protoplasts from leaves of well-fertilized barley (Hordeum vulgare L.) plants contained amino acids at concentrations as high as 120 millimoles per liter. With the exception of glutamic acid, which is predominantly localized in the cytoplasm, a major part of all other amino acids was contained inside the large central vacuole. Alanine, leucine, and glutamine are the dominant vacuolar amino acids in barley. Their transport into isolated vacuoles was studied using {sup 14}C-labeled amino acids. Uptake was slow in the absence of ATP. A three- to sixfold stimulation of uptake was observed after addition of ATP or adenylyl imidodiphosphate an ATP analogue not being hydrolyzed by ATPases. Other nucleotides were ineffective in increasing the rate of uptake. ATP-Stimulated amino acid transport was not dependent on the transtonoplast pH or membrane potential. p-Chloromercuriphenylsulfonic acid and n-ethyl maleimide increased transport independently of ATP. Neutral amino acids such as valine or leucine effectively decreased the rate of alanine transport. Glutamine and glycine were less effective or not effective as competitive inhibitors of alanine transport. The results indicate the existence of a uniport translocator specific for neutral or basic amino acids that is under control of metabolic effectors.

Dietz, K.J.; Jaeger, R.; Kaiser, G.; Martinoia, E. (Institut fuer Botanik and Pharmazeutische Biologie der Universitaet, Wuerzburg (Germany, F.R.))

1990-01-01

322

Valine and phenylalanine as precursors in the biosynthesis of alkamides in Acmella radicans.  

PubMed

Acmella radicans (Asteraceae) produces at least seven alkamides, most with either an isobutyl- or phenylethyl group as the amine moiety. These moieties suggest that the amino acids valine and phenylalanine are the biosynthetic precursors of these alkamides. On the basis of labeled feeding experiments using either L-[2H8]valine or L-[2H8]phenylalanine we present evidence for the involvement of these two amino acids in the biosynthesis of (2E,6Z,8E)-N-isobutyl-2,6,8-decatrienamide (affinin) (1), (2Z,4E)-N-(2-phenylethyl)-2,4-octadienamide (2), (2E)-N-(2-phenylethyl)-nona-2-en-6,8-diynamide (3), and 3-phenyl-N-(2-phenylethyl)-2-propenamide (4). Alkamides were isolated from young A. radicans plants and analyzed by gas chromatography-mass spectrometry (GC-MS). Additionally, in cell free in vitro experiments based on isobutyl and phenylethylamide biosynthesis, using a colorimetric assay and GC-MS, valine and phenylalanine decarboxylase activities were assayed in the soluble extract of A. radicans leaves. PMID:21815426

Cortez-Espinosa, Nancy; Aviña-Verduzco, Judit A; Ramírez-Chávez, Enrique; Molina-Torres, Jorge; Ríos-Chávez, Patricia

2011-06-01

323

Indicator assay for amino acid decarboxylases.  

PubMed

Indicator assays have been devised for glutamate decarboxylase and arginine decarboxylase as models for a general procedure for amino acid decarboxylases. Since the decarboxylation results in the absorption of a proton in the pH range of maximum enzymatic activity, the change in absorbance of an acid-base indicator can be used to follow the progress of the reaction. For glutamate decarboxylase, the substrate was used as the buffer, and 1-1'-diethyl-2-2'-cyanine iodide was used as the indicator. For arginine decarboxylase, acetate was used as the buffer, and bromcresol green was used as the indicator. The change in absorption with extent of reaction is linear if the indicator pK is equal to the buffer pK. PMID:2817382

Rosenberg, R M; Herreid, R M; Piazza, G J; O'Leary, M H

1989-08-15

324

Amino acid analysis for meat protein evaluation.  

PubMed

The Food Safety and Inspection Service procedure for determination of essential amino acid content of mechanically processed products from red meat animals and poultry is based on hydrolysis of a powder prepared by blending samples in acetone-chloroform. The hydrolysis procedure incorporates thioglycolic acid to prevent loss of tryptophan. Aliquots of prepared hydrolysates are injected into a liquid chromatographic system, using gradient elution on an ion-exchange column for separation. The system also uses post-column hypochlorite oxidation coupled with orthophthalaldehyde reagent and fluorescence detection. Modification of the elution program allows concurrent determination of tryptophan with minimal added cost. Chromatograms from beef, pork, and poultry products show adequate separation and quantitation of beta-alanine, 1-methyl-histidine, and 3-methyl-histidine, indicating that the procedure could be used to estimate muscle content of products. A colorimetric procedure for assay of hydroxyproline was introduced and validated as an adjunct method for protein quality estimation. PMID:3558283

Ashworth, R B

1987-01-01

325

The Component Combined Amino Acids of Some Marine Phytoplankton Species  

Microsoft Academic Search

Gas-liquid and thin-layer chromatography have been used for the determina­ tion of 25 amino acids in the hydrolysates of 25 species of marine phytoplankton which had been grown in Erd-Schreiber medium. The general pattern of their distribution agrees with that found by earlier workers; the principal amino acids being glutamic acid, alanine, leucine and aspartic acids. Small amounts of 2-amino­

Y. K. Chau; L. Chuecas; J. P. Riley

1967-01-01

326

Novel class of amino acid antagonists at non-N-methyl-D-aspartic acid excitatory amino acid receptors. Synthesis, in vitro and in vivo pharmacology, and neuroprotection  

Microsoft Academic Search

The isoxazole amino acid 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl) propionic acid (AMPA) (1), which is a highly selective agonist at the AMPA subtype of excitatory amino acid (EAA) receptors, has been used as a lead for the development of two novel EAA receptor antagonists. One of the compounds, 2-amino-3-(3-(carboxymethoxy)-5-methylisoxazol-4-yl)propionic acid (AMOA, 7), was synthesized via O-alkylation by ethyl chloroacetate of the amino acid protected

Povl Krogsgaard-Larsen; John W. Ferkany; Elsebet O. Nielsen; Ulf Madsen; Bjarke Ebert; Joergen S. Johansen; Nils H. Diemer; Torben Bruhn; David T. Beattie; David R. Curtis

1991-01-01

327

A reexamination of amino acids in lunar soil  

NASA Technical Reports Server (NTRS)

Amino acids in lunar soils provide an important indicator of the level of prebiotic organic compounds on the moon. The results provide insight into the chemistry of amino acid precursors, and furthermore, given the flux of carbonaceous material to the moon, we can evaluate the survival of organics upon impact. The amino acid contents of both hydrolyzed and unhydrolyzed hot-water extracts of Apollo 17 lunar soil were determined using ophthaldialdehyde/N-acetyl cysteine (OPA/NAC) derivatization followed by HPLC analysis. Previous studies of lunar amino acids were inconclusive, as the technique used (derivatization with ninhydrin followed by HPLC analysis) was unable to discriminate between cosmogenic amino acids and terrestrial contaminants. Cosmogenic amino acids are racemic, and many of the amino acids found in carbonaceous meteorites such as Murchison, i.e., alpha-amino-i-butyric acid (aib), are extremely rare on Earth. The ninhydrin method does not distinguish amino acid enantiomers, nor does it detect alpha-alkyl amino acids such as aib, whereas the OPA/NAC technique does both.

Brinton, K. L. F.; Bada, J. L.; Arnold, J. R.

1993-01-01

328

A review of the role of acid-base balance in amino acid nutrition  

Microsoft Academic Search

ABSTRACT Acid-base balance and amino acid metabolism are intimately related. Changes in acid-base balance influence the metabolic fate of many amino acids. Also, acid-base homeostasis is achieved in part by alteration of amino acid metabolism, not only in the kidney, but also in liver, muscle and splanchnic tissue. Glutamine is the primary amino acid involved in renal ammonia- genesis, a

J. F. Patience; J. E Patience

2010-01-01

329

Synthesis, Chemical and Enzymatic Hydrolysis, and Aqueous Solubility of Amino Acid Ester Prodrugs of 3-Carboranyl Thymidine Analogues for Boron Neutron Capture Therapy of Brain Tumors  

PubMed Central

Various water-soluble L-valine-, L-glutamate-, and glycine ester prodrugs of two 3-Carboranyl Thymidine Analogues (3-CTAs), designated N5 and N5-2OH, were synthesized for Boron Neutron Capture Therapy (BNCT) of brain tumors since the water solubilities of the parental compounds proved to be insufficient in preclinical studies. The amino acid ester prodrugs were prepared and stored as hydrochloride salts. The water solubilities of these amino acid ester prodrugs, evaluated in phosphate buffered saline (PBS) at pH 5, pH 6 and pH 7.4, improved 48 to 6600 times compared with parental N5 and N5-2OH. The stability of the amino acid ester prodrugs was evaluated in PBS at pH 7.4, Bovine serum, and Bovine cerebrospinal fluid (CSF). The rate of the hydrolysis in all three incubation media depended primarily on the amino acid promoiety and, to a lesser extend, on the site of esterification at the deoxyribose portion of the 3-CTAs. In general, 3'-amino acid ester prodrugs were less sensitive to chemical and enzymatic hydrolysis than 5'-amino acid ester prodrugs and the stabilities of the latter decreased in the following order: 5'-valine > 5'-glutamate > 5'-glycine. The rate of the hydrolysis of the 5'-amino acid ester prodrugs in Bovine CSF was overall higher than in PBS and somewhat lower than in Bovine serum. Overall, 5'-glutamate ester prodrug of N5 and the 5'-glycine ester prodrugs of N5 and N5-2OH appeared to be the most promising candidates for preclinical BNCT studies.

Hasabelnaby, Sherifa; Goudah, Ayman; Agarwal, Hitesh K.; Abd alla, Mosaad S. M.; Tjarks, Werner

2012-01-01

330

Analytical continuation in coupling constant method; application to the calculation of resonance energies and widths for organic molecules: Glycine, alanine and valine and dimer of formic acid  

NASA Astrophysics Data System (ADS)

The method of analytic continuation in the coupling constant (ACCC) in combination with use of the statistical Padé approximation is applied to the determination of resonance energy and width of some amino acids and formic acid dimer. Standard quantum chemistry codes provide accurate data which can be used for analytic continuation in the coupling constant to obtain the resonance energy and width of organic molecules with a good accuracy. The obtained results are compared with the existing experimental ones.

Papp, P.; Matej?ík, Š.; Mach, P.; Urban, J.; Paidarová, I.; Horá?ek, J.

2013-06-01

331

Amino acid adsorption by clay minerals in distilled water  

NASA Astrophysics Data System (ADS)

The adsorption of 15 protein amino acids from dilute (~ 10 ?M) distilled water solutions onto organic-free kaolinite and montmorillonite clay minerals (1 wt% suspensions) was determined at room temperature over a 48 hour period. The systems came to steady state within 2 hours. Basic (positively charged) amino acids were strongly adsorbed (40-80% removal) by both clay minerals. Neutral (uncharged) amino acids were taken up appreciably (10-15%) by montmorillonite, but little if any (<5%) by kaolinite. Acidic (negatively charged) amino acids were adsorbed (20-35%) only by kaolinite. These adsorption patterns appear to be related in part to electrostatic interactions between the clay mineral surfaces and the different amino acid types. The measured extents and selectivities of adsorption onto these clay minerals are sufficiently great to potentially affect the distributions and reactions of free amino acids in natural environments.

Hedges, John I.; Hare, P. E.

1987-02-01

332

One-pot synthesis of 2-isopropyl-3-benzyl-1,3-thiazolidin-4-ones and 2-phenyl-3-isobutyl-1,3-thiazolidin-4-ones from valine, arenealdehydes and mercaptoacetic acid  

Microsoft Academic Search

A three-component one-pot synthesis of 2-isopropyl-3-benzyl-1,3-thiazolidin-4-ones and 2-phenyl-3-isobutyl-1,3-thiazolidin-4-ones from valine, arenealdehydes and mercaptoacetic acid with good yields is reported. Characterization of products was generally achieved by NMR techniques and specifically for 2-isopropyl-3-(4-nitrobenzyl)-1,3-thiazolidin-4-one by X-ray crystallography.

Wilson Cunico; Claudia R. B. Gomes; Maria de Lourdes G. Ferreira; Liliane R. Capri; Marcio Soares; Solange M. S. V. Wardell

2007-01-01

333

The Effect of Keto-analogues of Essential Amino Acids in Severe Chronic Uremia  

PubMed Central

Alpha keto-analogues of valine, leucine, isoleucine, methionine, phenylalanine, and (in one instance) tryptophan and histidine, along with the remaining essential amino acids, were administered orally to 10 patients with severe chronic uremia fed a diet low in protein but adequate in calories. Ketoacid dosage varied from 6 to 14 g daily, as sodium or calcium salts. Net nitrogen intake, calculated as intake minus urinary protein nitrogen, averaged 1.8 g/day. The urea space was either estimated or measured with [14C]urea and daily changes in the body urea pool were calculated. Urea appearance was measured as the sum of urea excretion and the change in urea pool. If these ketoacids were converted to amino acids and utilized for protein synthesis, a fall in urea nitrogen appearance should occur. In five subjects, ketoacids were given for 15-18 days and then withdrawn. Urea nitrogen appearance increased 1.55 g/day on withdrawing ketoacids, and corrected nitrogen balance decreased by 1.73 g/day. In two other subjects ketoacid administration was followed, on two occasions each, by a period of administration of nine essential amino acids. In three of these four instances, urea appearance rose significantly with amino acids. In four patients studied at high blood urea levels, ketoacid treatment was relatively ineffective; two of these patients responded more favorably when studied again after peritoneal dialysis. One of these improved enough clinically to be managed as an out-patient for short intervals, despite virtual anuria. No accumulation of ketoacids in plasma or urine could be detected, and no toxicity was identified.

Walser, Mackenzie; Coulter, A. Will; Dighe, Shrikant; Crantz, Frank R.

1973-01-01

334

Synthesis of Essential Amino Acids from Their ?-Keto Analogues by Perfused Rat Liver and Muscle  

PubMed Central

Most essential amino acids can be replaced by their ?-keto-analogues in the diet. These ketoacids have therefore been proposed as substitutes for dietary protein. In order to determine their fate in tissues of normal animals, isolated rat liver and hindquarter (muscle) preparations were perfused with keto-analogues of valine, leucine, isoleucine, methionine, or phenylalanine. When perfused at 1.5-2.0 mM, all five compounds were utilized rapidly by the liver of 48-h starved rats, at rates varying from 49 to 155 ?mol/h per 200g rat. The corresponding amino acids appeared in the medium in significantly increased concentrations. Perfusion with phenylpyruvate also led to the appearance of tyrosine. Urea release was unaltered. Measurement of metabolite concentrations in freeze-clamped liver revealed two abnormalities, particularly at ketoacid concentrations of 5 mM or above: a large increase in ?-ketoglutarate, and a moderate to marked decrease in tissue glutamine. This decrease was quantitatively sufficient to account for nitrogen appearing in newly synthesized amino acids. Isolated hindquarters of fed rats were perfused with the same ketoacids at concentrations of 1.3-8.0 mM. All were utilized at rates varying from 1.4 to 7.0 ?mol/h per g muscle perfused. The corresponding amino acids were released at greatly increased rates. Alanine and glutamate levels fell in some perfusions, but the principal nitrogen donor in muscle was not identified; the content of glutamine in tissue, and its rate of release into the perfusate remained constant.

Walser, Mackenzie; Lund, Patricia; Ruderman, Neil B.; Coulter, A. W.

1973-01-01

335

Serum and adipose tissue amino Acid homeostasis in the metabolically healthy obese.  

PubMed

A subgroup of obese individuals, referred to as metabolically healthy obese (MHO), have preserved insulin sensitivity and a normal lipid profile despite being obese. The molecular basis for this improved cardiometabolic profile remains unclear. Our objective was to integrate metabolite and gene expression profiling to elucidate the molecular distinctions between MHO and metabolically unhealthy obese (MUO) phenotypes. A subset of individuals were selected from the Diabetes Risk Assessment study and classified into three groups using anthropometric and clinical measurements: lean healthy (LH), MHO, and MUO. Serum metabolites were profiled using gas chromatography coupled to mass spectrometry. Multivariate data analysis uncovered metabolites that differed between groups, and these were subsequently validated by capillary electrophoresis coupled to mass spectrometry. Subcutaneous adipose tissue (SAT) gene expression profiling using microarrays was performed in parallel. Amino acids were the most relevant class of metabolites distinguishing MHO from MUO individuals. Serum levels of glutamic acid, valine, and isoleucine were positively associated (i.e., LH < MHO < MUO) with homeostasis model assessment-insulin resistance (HOMA-IR) and glycated hemoglobin (HbA1c) values, while leucine was only correlated with HOMA-IR. The glutamine-to-glutamic acid ratio and glycine were inversely correlated (i.e., LH > MHO > MUO) with HbA1c values. Concomitantly, SAT gene expression profiling revealed that genes related to branched-chain amino acid catabolism and the tricarboxylic acid cycle were less down-regulated in MHO individuals compared to MUO individuals. Together, this integrated analysis revealed that MHO individuals have an intermediate amino acid homeostasis compared to LH and MUO individuals. PMID:24933025

Badoud, Flavia; Lam, Karen P; DiBattista, Alicia; Perreault, Maude; Zulyniak, Michael A; Cattrysse, Bradley; Stephenson, Susan; Britz-McKibbin, Philip; Mutch, David M

2014-07-01

336

Exploration of amino acid biomarkers in polar ice with the Mars Organic Analyzer  

NASA Astrophysics Data System (ADS)

A portable microfabricated capillary electrophoresis (CE) system named the Mars Organic Analyzer (MOA) has been developed to analyze fluorescently-labeled biomarkers including amino acids, amines, nucleobases, and amino sugars with the goal of life detection on Mars (1,2). This technology has also been shown to be effective in screening the formation of biogenic amines during fermentation (3). The MOA is a part of the Urey instrument package that has been selected for the 2016 European ExoMars mission by ESA. The identification of recent gully erosion sites, observations of ice on and beneath the surface of Mars, and the discovery of large reservoirs of sub-surface ice on Mars point to water-ice as an important target for astrobiological analyses. In addition, the ice samples on the Moon, Mercury, Europa and Enceladus are of interest due to the possibility that they may contain information on biogenic material relevant to the evolution of life. We explore here the use of the MOA instrument for the analysis of amino acids in polar ice samples. The amino acids valine, alanine/serine, glycine, glutamic acid, and aspartic acid were found in the parts-per-billion range from Greenland ice-core samples. Chiral analysis of these samples yielded D/L ratios of 0.51/0.09 for alanine/serine and 0.14/0.06 for aspartic acid. Individual amino acids in the parts-per-trillion range were found in Antarctic ice samples collected from the surface of a meteorite collection area. The distinct amino acid and amine content of these samples indicates that further biomarker characterization of ice samples as a function of sampling location, depth, and structural features will be highly informative. The rapid sensitive analysis capabilities demonstrated here establish the feasibility of using the MOA to analyze the biomarker content of ice samples in planetary exploration. 1. Skelley, A. M.; Scherer, J. R.; Aubrey, A. D.; Grover, W. H.; Ivester, R. H. C., Ehrenfreund, P.; Grunthaner, F. J.; Bada, J. L.; Mathies, R. A. PNAS, 2005, 192, 1041. 2. Skelley, A. M., Cleaves, H. J., Jayarajah, C. N., Bada, J. L. and Mathies, R. A., Astrobiology 2006, 6, 824. 3. Jayarajah, C.N., Skelley, A.M., Fortner, A.D., and Mathies, R.A., Anal. Chem. 2007, 79, 21, 8162.

Jayarajah, C.; Botta, O.; Aubrey, A.; Parker, E.; Bada, J.; Mathies, R.

2009-05-01

337

Catalytic hydrogenation of amino acids to amino alcohols with complete retention of configuration.  

PubMed

Rh-MoOx/SiO2 is an effective heterogeneous catalyst for selective hydrogenation of amino acids to amino alcohols in a water solvent. MoOx modification of Rh drastically enhanced the activity and improved the selectivity and ee. Various amino alcohols were obtained in high yields (90-94%) with complete retention of configuration. PMID:24824793

Tamura, Masazumi; Tamura, Riku; Takeda, Yasuyuki; Nakagawa, Yoshinao; Tomishige, Keiichi

2014-05-27

338

Unprecedented concentrations of indigenous amino acids in primitive CR meteorites  

NASA Astrophysics Data System (ADS)

CR meteorites are among the most primitive meteorites. We have performed pioneering work determining the compositional characteristics of amino acids in this type of carbonaceous chondrites. We report the first measurements of amino acids in Antarctic CR meteorites, two of which show the highest amino acid concentrations ever found in a chondrite. We have analyzed the amino acid content of the Antarctic CRs EET92042, GRA95229 and GRO95577 using high performance liquid chromatography with UV fluorescence detection (HPLC-FD) and gas chromatography-mass spectrometry (GC-MS). Additionally, compound-specific carbon isotopic measurements for most of the individual amino acids from the EET92042 and GRA95229 meteorites were achieved by gas chromatography-combustion-isotope ratio mass spectrometry (GC-C-IRMS). Our data show that EET92042 and GRA95229 are the most amino acid-rich chondrites ever analyzed, with total amino acid concentrations of 180 and 249 parts-per-million (ppm), respectively. GRO95577, however, is depleted in amino acids (<1 ppm). The most abundant amino acids present in the EET92042 and GRA95229 meteorites are the ?-amino acids glycine, isovaline, ?-aminoisobutyric acid (?-AIB), and alanine, with ? 13 C values ranging from +31.6% to +50.5%. The highly enriched carbon isotope results together with racemic enantiomeric ratios determined for most amino acids indicate that primitive organic matter was preserved in these meteorites. In addition, the relative abundances of ?-AIB and ?-alanine amongst Antarctic CR meteorites appear to correspond to the degree of aqueous alteration on their respective parent body. Investigating the abundances and isotopic composition of amino acids in primitive chondrites helps to understand the role of meteorites as a source of extraterrestrial prebiotic organic compounds to the early Earth.

Ehrenfreund, Pascale; Martins, Zita; Alexander, Conel; Orzechowska, Grazyna; Fogel, Marylin

339

Plasma amino acid quantitation using gas chromatography chemical ionization mass spectrometry and 13C amino acids as internal standards.  

PubMed

A specific and sensitive method for the quantitation of 16 alpha amino acids has been developed. The technique employed uses methane chemical ionization gas chromatography mass spectrometry of the carboxy-n-butyl, N-trifluoroacetyl amino acid derivatives. A commercial 13C amino acid mixture provided individual internal standards for 14 alpha amino acids. A computer controlled quadrupole mass spectrometer was used for selected ion monitoring of those ions characteristic of each N-trifluoroacetyl amino acid/13C amino acid pair. A BASIC computer program located peak maxima and background intensities in each selected ion recording. Standard curves for each amino acid/13C amino acid pair were utilized by the program to calculate the plasma concentration of each detected amino acid. The total instrumental analysis occupied 30 min with sample preparation and derivatization accounting for an additional 2 h. Based on the detection of known amounts of standard amino acids the method will quantitate at the 1-5 nanogram level of detection. PMID:749957

Kingston, E E; Duffield, A M

1978-11-01

340

THIN-LAYER SEPARATION OF CITRIC ACID CYCLE INTERMEDIATES, LACTIC ACID, AND THE AMINO ACID TAURINE  

EPA Science Inventory

This paper describes a two-dimensional mixed-layer method for separating citric acid cycle intermediates, lactic acid and the amino acid taurine. The method cleanly separates all citric acid cycle intermediates tested, excepting citric acid and isocitric acid. The solvents are in...

341

Geochemistry of amino acids in shells of the clam Saxidomus  

USGS Publications Warehouse

Concentrations of amino acids and their corresponding d l enantiomeric ratios have been measured in shells of the bivalve mollusk Saxidomus from eleven localities, ranging in age from modern to probably more than 500,000 yr, along the Pacific coast of North America. Natural logarithms of amino acid concentrations correlate well with d l ratios, and the relationship provides a possible guide to the selection of fossils for use in amino acid dating. The relative order of the extents of racemization of amino acids at any given time appears to change with increasing sample age. Application of the amino acid dating method to shells from Whidbey Island, Washington, yields an age of about 80,000 yr, in contrast to the previously determined radiocarbon age of 36,000 yr which was measured on some shell carbonate and considered a minimum age. The amino acid age is compatible with the geologic record in the area. ?? 1980.

Kvenvolden, K. A.; Blunt, D. J.; McMenamin, M. A.; Straham, S. E.

1980-01-01

342

[Amino acid sequence of anionic protease inhibitors from buckwheat seeds].  

PubMed

Complete amino acid sequence of IT1 protease inhibitor and partial amino acid sequences of IT2 and IT4 protease inhibitors from buckwheat Fagopyrum esculentum Moench seeds were determined by automatic Edman degradation and mass spectrometry. IT1 inhibitor comprises 69 amino acid residues and its molecular mass is 7743.8 D. N-terminal 48 amino acid residues of IT2 inhibitor are identical to similar sequence of IT1 inhibitor. The sequence of 10 amino acid residues of IT4 inhibitor is completely identical to a part of the sequence of IT1 inhibitor C-terminally adjacent to its active site. Analysis of amino acid sequences of IT1, IT2 and IT4 inhibitors suggests that the proteins are the members of the potato proteinase inhibitor 1 family and include Arg-Asp residues in their active site. PMID:9011225

Belozerski?, M A; Dunaevski?, Ia E; Musaliamov, A Kh; Egorov, Ts A

1996-10-01

343

Survival of Amino Acids in Micrometeorites During Atmospheric Entry  

NASA Technical Reports Server (NTRS)

The delivery of amino acids by micrometeorites to the early Earth during the period of heavy bombardment could have been a significant source of the Earth's prebiotic amino acid inventory provided that these organic compounds survived atmospheric entry heating. To investigate the sublimation of amino acids from a micrometeorite analog at elevated temperature, grains from the CM-type carbonaceous chondrite Murchison were heated to 550 C inside a glass sublimation apparatus (SA) under reduced pressure. The sublimed residue that had collected on the cold finger of the SA after heating was analyzed for amino acids by HPLC. We found that when the temperature of the meteorite reached approx. 150 C, a large fraction of the amino acid glycine had vaporized from the meteorite, recondensed onto the end of the SA cold finger, and survived as the rest of the grains heated to 550 C. alpha-Aminoisobutryic acid and isovaline, which are two of the most abundant non-protein amino acids in Murchison, did not sublime from the meteorite and were completely destroyed during the heating experiment. Our experimental results suggest that sublimation of glycine present in micrometeorite grains may provide a way for this amino acid to survive atmospheric entry heating at temperatures less than 550 C; all other amino acids apparently are destroyed. Key Words: Amino acids-Exogenous delivery-Micrometeorites-Sublimation.

Glavin, Daniel P.; Bada, Jeffrey L.

2003-01-01

344

Mutagenesis studies on the sensitivity of Escherichia coli acetohydroxyacid synthase II to herbicides and valine.  

PubMed Central

Acetohydroxyacid synthase (EC 4.1.3.18, also known as acetolactate synthase) isoenzyme II from Escherichia coli is inhibited by sulphonylurea and imidazolinone herbicides, although it is much less sensitive than the plant enzyme. This isoenzyme is also unusual in that it is not inhibited by valine. Mutating S100 (Ser(100) in one-letter amino acid notation) of the catalytic subunit to proline increases its sensitivity to sulphonylureas, but not to imidazolinones. Mutating P536 to serine, as found in the plant enzyme, had little effect on the properties of the enzyme. Mutating E14 of the regulatory subunit to glycine, either alone or in combination with the H29N (His(29)-->Asn) change, did not affect valine-sensitivity.

Lee, Y T; Duggleby, R G

2000-01-01

345

Screening for defects of branched-chain amino acid metabolism  

Microsoft Academic Search

Screening for defects of branched-chain amino acid metabolism is a sequential process involving clinical evaluation of the patient, plasma carnitine determination, urinary organic acid analysis, and enzyme studies in cultured or isolated peripheral cells. This report will summarize clinical and metabolite features and enzymological methods available for the diagnosis of the more common defects of branchedchain amino acid metabolism, including

K. Michael Gibson; Carol F. Lee; Georg F. Hoffmann

1994-01-01

346

Comparative Genomics of Regulation of Fatty Acid and Branched-chain Amino Acid Utilization in Proteobacteria  

SciTech Connect

Bacteria can use branched-chain amino acids (ILV, i.e. isoleucine, leucine, valine) and fatty acids (FA) as sole carbon and energy sources convering ILV into acetyl-CoA, propanoyl-CoA and propionyl-CoA, respectively. In this work, we used the comparative genomic approach to identify candidate transcriptional factors and DNA motifs that control ILV and FA utilization pathways in proteobacteria. The metabolic regulons were characterized based on the identification and comparison of candidate transcription factor binding sites in groups of phylogenetically related genomes. The reconstructed ILV/FA regulatory network demonstrates considerable variability and involves six transcriptional factors from the MerR, TetR and GntR families binding to eleven distinct DNA motifs. The ILV degradation genes in gamma- and beta-proteobacteria are mainly regulated by anovel regulator from the MerR family (e.g., LiuR in Pseudomonas aeruginosa) (40 species), in addition, the TetR-type regulator LiuQ was identified in some beta-proteobacteria (8 species). Besides the core set of ILV utilization genes, the LiuR regulon in some lineages is expanded to include genes from other metabolic pathways, such as the glyoxylate shunt and glutamate synthase in the Shewanella species. The FA degradation genes are controlled by four regulators including FadR in gamma-proteobacteria (34 species), PsrA in gamma- and beta-proteobacteria (45 species), FadP in beta-proteobacteria (14 species), and LiuR orthologs in alpha-proteobacteria (22 species). The remarkable variability of the regulatory systems associated with the FA degradation pathway is discussed from the functional and evolutionary points of view.

Kazakov, Alexey E.; Rodionov, Dmitry A.; Arkin, Adam Paul; Dubchak, Inna; Gelfand, Mikhail S.; Alm, Eric

2008-10-31

347

Comparative Genomics of Regulation of Fatty Acid and Branched-Chain Amino Acid Utilization in Proteobacteria? †  

PubMed Central

Bacteria can use branched-chain amino acids (ILV, i.e., isoleucine, leucine, valine) and fatty acids (FAs) as sole carbon and energy sources converting ILV into acetyl-coenzyme A (CoA), propanoyl-CoA, and propionyl-CoA, respectively. In this work, we used the comparative genomic approach to identify candidate transcriptional factors and DNA motifs that control ILV and FA utilization pathways in proteobacteria. The metabolic regulons were characterized based on the identification and comparison of candidate transcription factor binding sites in groups of phylogenetically related genomes. The reconstructed ILV/FA regulatory network demonstrates considerable variability and involves six transcriptional factors from the MerR, TetR, and GntR families binding to 11 distinct DNA motifs. The ILV degradation genes in gamma- and betaproteobacteria are regulated mainly by a novel regulator from the MerR family (e.g., LiuR in Pseudomonas aeruginosa) (40 species); in addition, the TetR-type regulator LiuQ was identified in some betaproteobacteria (eight species). Besides the core set of ILV utilization genes, the LiuR regulon in some lineages is expanded to include genes from other metabolic pathways, such as the glyoxylate shunt and glutamate synthase in Shewanella species. The FA degradation genes are controlled by four regulators including FadR in gammaproteobacteria (34 species), PsrA in gamma- and betaproteobacteria (45 species), FadP in betaproteobacteria (14 species), and LiuR orthologs in alphaproteobacteria (22 species). The remarkable variability of the regulatory systems associated with the FA degradation pathway is discussed from functional and evolutionary points of view.

Kazakov, Alexey E.; Rodionov, Dmitry A.; Alm, Eric; Arkin, Adam Paul; Dubchak, Inna; Gelfand, Mikhail S.

2009-01-01

348

Amino acids of the Murchison meteorite. II - Five carbon acyclic primary beta-, gamma-, and delta-amino alkanoic acids  

NASA Technical Reports Server (NTRS)

The five-carbon acyclic primary beta, gamma, and delta amino alkanoic acids of the Murchison meteorite are studied using gas chromatography-mass spectrometry and ion exchange chromatography. The chromatograms reveal that alpha is the most abundant monoamino alkanoic acid followed by gamma and beta, and an exponential increase in the amount of amino acid is observed as the carbon number increases in the homologous series. The influence of frictional heating, spontaneous thermal decomposition, and radiation of the synthesis of amino acids is examined. The data obtained support an amino acid synthesis process involving random combination of single-carbon precursors.

Cronin, J. R.; Pizzarello, S.; Yuen, G. U.

1985-01-01

349

Utilization of ?-Keto and ?-Hydroxy Analogues of Valine by the Growing Rat  

PubMed Central

When 70-80-g male albino rats eat a diet furnishing daily requirement of valine for optimal growth (70 ?mol/g) and all other nutrients (“complete diet”), they gain weight at an average rate of 3.0 g/100 g body wt/day. When valine is removed, they lose weight at an average 2.1 g/100 g body wt/day. The growth retardation is improved or corrected by adding valine to the diet, daily weight gain being proportional to dietary valine content over a range of 0-70 ?mol/g. Addition of ?-ketoisovaleric acid instead of valine to the valine-free diet also improves or corrects the growth failure. Percent efficiency of ?-ketoisovaleric acid as a substitute for valine was calculated as: 100 × (micromole valine per gram diet required to produce specified growth response)/(micromole ?-ketoisovaleric acid per gram diet required to produce the same response). Efficiency of the substitution is inversely related to dietary content of the keto analogue, being 80% when diet contains 17.5 ?mol/g (molar equivalent of ¼ the daily requirement of valine), and 37% when diet provides 140 ?mol/g (molar equivalent of twice the daily requirement of valine). ?-Hydroxyisovaleric acid also substitutes for valine. Efficiency of the substitution at the single ration tested, 70 ?mol/g diet, is 45%, similar to that for the keto analogue under the same conditions. When [1-14C]?-ketoisovaleric acid is injected intravenously, 30-80% of the administered radioactivity is exhaled as 14CO2 within 24 h. This finding suggests that inefficiency of ?-ketoisovaleric acid as a substitute for valine results in part from degradation of the keto acid to isobutyric acid by branched chain dehydrogenase-decarboxylase. Oral administration of neomycin, polymyxin, and bacitracin reduces efficiency of ?-ketoisovaleric acid as a substitute for valine by ¼-½. This effect suggests that transamination of the keto acid may be performed in part by gastrointestinal microbes.

Chawla, Rajender K.; Rudman, Daniel

1974-01-01

350

Amino acid transport in the renal proximal tubule  

Microsoft Academic Search

Summary.   In the kidney the proximal tubule is responsible for the uptake of amino acids. This occurs via a variety of functionally\\u000a and structurally different amino acid transporters located in the luminal and basolateral membrane. Some of these transporters\\u000a show an ion-dependence (e.g. Na+, Cl? and K+) or use an H+-gradient to drive transport. Only a few amino acid transporters

T. Gonska; J. R. Hirsch; E. Schlatter

2000-01-01

351

Peptidology: short amino acid modules in cell biology and immunology  

Microsoft Academic Search

Summary.  Short amino acid motifs, either linear sequences or discontinuous amino acid groupings, can interact with specific protein\\u000a domains, so exerting a central role in cell adhesion, signal transduction, hormone activity, regulation of transcript expression,\\u000a enzyme activity, and antigen-antibody interaction. Here, we analyze the literature for such critical short amino acid motifs\\u000a to determine the minimal peptide length involved in biologically

G. Lucchese; A. Stufano; B. Trost; A. Kusalik; D. Kanduc

2007-01-01

352

Sulfur-Containing Amino Acid Metabolism in Parasitic Protozoa  

Microsoft Academic Search

Sulfur-containing amino acids play indispensable roles in a wide variety of biological activities including protein synthesis, methylation, and biosynthesis of polyamines and glutathione. Biosynthesis and catabolism of these amino acids need to be carefully regulated to achieve the requirement of the above-mentioned activities and also to eliminate toxicity attributable to the amino acids. Genome-wide analyses of enzymes involved in the

Tomoyoshi Nozaki; Vahab Ali; Masaharu Tokoro

2005-01-01

353

GLC of amino acids - A survey of contamination.  

NASA Technical Reports Server (NTRS)

Analyses of biological substances and geochemical samples, of both terrestrial and extraterrestrial origin, are reported for amino acids at the 1-10 nanogram per gram level achieved by gas-liquid and ion-exchange chromatographic methods. These studies have shown that nanogram quantities of amino acids, present in water extracts of geochemical samples or in other samples of low amino acid concentration, can be successfully determined only if the researcher is well aware of the possible sources of contamination.

Rash, J. J.; Gehrke, C. W.; Kuo, K. C.; Kvenvolden, K. A.; Stalling, D. L.; Zumwalt, R. W.

1972-01-01

354

Synthesis of alpha-amino acids  

DOEpatents

A method is described for synthesizing alpha amino acids proceeding through novel intermediates of the formulas: R[sub 1]R[sub 2]C(OSOCl)CN, R[sub 1]R[sub 2]C(Cl)CN and [R[sub 1]R[sub 2]C(CN)O][sub 2]SO wherein R[sub 1] and R[sub 2] are each selected from hydrogen monovalent substituted and unsubstituted hydrocarbon radicals of 1 to 10 carbon atoms. The use of these intermediates allows the synthesis steps to be exothermic and results in an overall synthesis method which is faster than the synthesis methods of the prior art. No Drawings

Davis, J.W. Jr.

1983-01-25

355

Nitrogen Sparing Induced by a Mixture of Essential Amino Acids Given Chiefly as Their Keto-Analogues during Prolonged Starvation in Obese Subjects  

PubMed Central

11 normal obese subjects were fasted for 33 days. In five, who served as controls, urine urea nitrogen excretion remained constant for 2 wk thereafter. The other six were given seven daily infusions containing 6-8 mmol each of the ?-keto-analogues of valine, leucine, isoleucine, phenylalanine, and methionine (as sodium salts) plus 3-4 mmol each of the remaining essential amino acids (lysine, threonine, tryptophan, and histidine). Rapid amination of the infused ketoacids occurred, as indicated by significant increases in plasma concentrations of valine, leucine, isoleucine, alloisoleucine, phenylalanine, and methionine. Glutamine, glycine, serine, glutamate, and taurine fell significantly. Blood glucose, ketone bodies, plasma free fatty acids, and serum immunoreactive insulin concentrations were unaltered. Urine urea nitrogen fell from 1.46 to 0.89 g/day on the last day of infusions; 5 days later it was still lower (0.63 g/day) and in two subjects studied for 9 and 17 days postinfusion it remained below preinfusion control values. Urine ammonia, creatinine, and uric acid were unaltered. Nitrogen balance became less negative during and after infusions. The results indicate that this mixture of essential amino acids and their keto-analogues facilitates nitrogen sparing during prolonged starvation, in part by conversion of the ketoacids to amino acids and in part by altering mechanisms of nitrogen conservation. The latter effect persists after the ketoacids are metabolized.

Sapir, Daniel G.; Owen, Oliver E.; Pozefsky, Thomas; Walser, Mackenzie

1974-01-01

356

Understanding and identifying amino acid repeats  

PubMed Central

Amino acid repeats (AARs) are abundant in protein sequences. They have particular roles in protein function and evolution. Simple repeat patterns generated by DNA slippage tend to introduce length variations and point mutations in repeat regions. Loss of normal and gain of abnormal function owing to their variable length are potential risks leading to diseases. Repeats with complex patterns mostly refer to the functional domain repeats, such as the well-known leucine-rich repeat and WD repeat, which are frequently involved in protein–protein interaction. They are mainly derived from internal gene duplication events and stabilized by ‘gate-keeper’ residues, which play crucial roles in preventing inter-domain aggregation. AARs are widely distributed in different proteomes across a variety of taxonomic ranges, and especially abundant in eukaryotic proteins. However, their specific evolutionary and functional scenarios are still poorly understood. Identifying AARs in protein sequences is the first step for the further investigation of their biological function and evolutionary mechanism. In principle, this is an NP-hard problem, as most of the repeat fragments are shaped by a series of sophisticated evolutionary events and become latent periodical patterns. It is not possible to define a uniform criterion for detecting and verifying various repeat patterns. Instead, different algorithms based on different strategies have been developed to cope with different repeat patterns. In this review, we attempt to describe the amino acid repeat-detection algorithms currently available and compare their strategies based on an in-depth analysis of the biological significance of protein repeats.

Nijveen, Harm

2014-01-01

357

Amino acid composition in parenteral nutrition: what is the evidence?  

PubMed Central

Purpose of review Complete parenteral nutrition solutions contain mixed amino acid products providing all nine essential amino acids and a varying composition of nonessential amino acids. Relatively little rigorous comparative efficacy research on altered parenteral nutrition amino acid composition has been published in recent years. Recent findings Limited data from randomized, double-blind, adequately powered clinical trials to define optimal doses of total or individual amino acids in parenteral nutrition are available. An exception is the growing number of studies on the efficacy of glutamine supplementation of parenteral nutrition or given as a single parenteral agent. Parenteral glutamine appears to confer benefit in selected patients; however, additional data to define optimal glutamine dosing and the patient subgroups who may most benefit from this amino acid are needed. Although some promising studies have been published, little data are available in the current era of nutrition support on the clinical efficacy of altered doses of arginine, branched chain amino acids, cysteine, or taurine supplementation of parenteral nutrition. Summary Despite routine use of parenteral nutrition, surprisingly little clinical efficacy data are available to guide total or specific amino acid dosing in adult and pediatric patients requiring this therapy. This warrants increased attention by the research community and funding agencies to better define optimal amino acid administration strategies in patient subgroups requiring parenteral nutrition.

Yarandi, Shadi S.; Zhao, Vivian M.; Hebbar, Gautam; Ziegler, Thomas R.

2011-01-01

358

Which Amino Acids Should Be Used in Prebiotic Chemistry Studies?  

NASA Astrophysics Data System (ADS)

The adsorption of amino acids on minerals and their condensation under conditions that resemble those of prebiotic earth is a well studied subject. However, which amino acids should be used in these experiments is still an open question. The main goal of this review is to attempt to answer this question. There were two sources of amino acids for the prebiotic earth: (1) exogenous—meaning that the amino acids were synthesized outside the earth and delivered to our planet by interplanetary dust particles (IDPs), meteorites, comets, etc. and (2) endogenous—meaning that they were synthesized on earth in atmospheric mixtures, hydrothermal vents, etc. For prebiotic chemistry studies, the use of a mixture of amino acids from both endogenous and exogenous sources is suggested. The exogenous contribution of amino acids to this mixture is very different from the average composition of proteins, and contains several non-protein amino acids. On the other hand, the mixture of amino acids from endogenous sources is seems to more closely resemble the amino acid composition of terrestrial proteins.

Zaia, Dimas A. M.; Zaia, Cássia Thaïs B. V.; de Santana, Henrique

2008-12-01

359

Metabolizable energy, nitrogen balance, and ileal digestibility of amino acids in quality protein maize for pigs  

PubMed Central

Background To compare the nutritional value and digestibility of five quality protein maize (QPM) hybrids to that of white and yellow maize, two experiments were carried out in growing pigs. In experiment 1, the energy metabolizability and the nitrogen balance of growing pigs fed one of five QPM hybrid diets were compared against those of pigs fed white or yellow maize. In experiment 2, the apparent and standardized ileal digestibility (AID and SID, respectively) of proteins and amino acids from the five QPM hybrids were compared against those obtained from pigs fed white and yellow maize. In both experiments, the comparisons were conducted using contrasts. Results The dry matter and nitrogen intakes were higher in the pigs fed the QPM hybrids (P?valine, phenylalanine, and methionine were lower in the QPM diets than those of maize (white and yellow) (all P?valine, phenylalanine, glutamic acid, serine, alanine, tyrosine, and proline (P?

2014-01-01

360

Branched-chain amino acids and ammonia metabolism in liver disease: therapeutic implications.  

PubMed

The rationale for recommendation of branched-chain amino acids (BCAA; valine, leucine, and isoleucine) in treatment of liver failure is based on their unique pharmacologic properties, stimulatory effect on ammonia detoxification to glutamine (GLN), and decreased concentrations in liver cirrhosis. Multiple lines of evidence have shown that the main cause of the BCAA deficiency in liver cirrhosis is their consumption in skeletal muscle for synthesis of glutamate, which acts as a substrate for ammonia detoxification to GLN and that the BCAA administration to patients with liver failure may exert a number of positive effects that may be more pronounced in patients with marked depression of BCAA levels. On the other hand, due to the stimulatory effect of BCAA on GLN synthesis, BCAA supplementation may lead to enhanced ammonia production from GLN breakdown in the intestine and the kidneys and thus exert harmful effects on the development of hepatic encephalopathy. Therefore, to enhance therapeutic effectiveness of the BCAA in patients with liver injury, their detrimental effect on ammonia production, which is negligible in healthy people and/or patients with other disorders, should be avoided. In treatment of hepatic encephalopathy, simultaneous administration of the BCAA (to correct amino acid imbalance and promote ammonia detoxification to GLN) with ?-ketoglutarate (to inhibit GLN breakdown to ammonia in enterocytes) and/or phenylbutyrate (to enhance GLN excretion by the kidneys) is suggested. Attention should be given to the type of liver injury, gastrointestinal bleeding, signs of inflammation, and the dose of BCAA. PMID:23756281

Holecek, Milan

2013-10-01

361

Factors regulating amino acid release from extrasplanchnic tissues in the rat. Interactions of alanine and glutamine.  

PubMed Central

1. Factors regulating the release of alanine and glutamine in vivo were investigated in starved rats by removing the liver from the circulation and monitoring blood metabolite changes for 30 min. 2. Alanine and glutamine were the predominant amino acids released into the circulation in this preparation. 3. Dichloroacetate, an activator of pyruvate dehydrogenase, inhibited net alanine release: it also interfered with the metabolism of the branched-chain amino acids valine, leucine and isoleucine. 4. L-Cycloserine, an inhibitor of alanine aminotransferase, decreased alanine accumulation by 80% after functional hepatectomy, whereas methionine sulphoximine, an inhibitor of glutamine synthetase, decreased glutamine accumulation by the same amount. 5. It was concluded that: (a) the alanine aminotransferase and the glutamine synthetase pathways respectively were responsible for 80% of the alanine and glutamine released into the circulation by the extrasplanchnic tissues, and extrahepatic proteolysis could account for a maximum of 20%; (b) alanine formation by the peripheral tissues was dependent on availability of pyruvate and not of glutamate; (c) glutamate availability could influence glutamine formation subject, possibly, to renal control.

Blackshear, P J; Holloway, P A; Alberti, K G

1975-01-01

362

Attenuation of the protein wasting associated with bed rest by branched-chain amino acids  

NASA Technical Reports Server (NTRS)

Bed rest is generally accepted as being an appropriate ground-based model for human spaceflight. The objectives of this study were to test the hypothesis that increasing the amount of branched-chain amino acids (BCAAs) in the diet could attenuate the protein loss associated with bed rest. Nineteen healthy subjects were randomized into two groups according to diet. During the 6 d of bed rest, the diets were supplemented with either 30 mmol/d each of three non-essential amino acids, glycine, serine, and alanine (control group), or with 30 mmol/d each of the BCAAs, leucine, isoleucine, and valine (BCAA group). Nutrition was supplied as a commercially available defined formula diet at a rate of 1.3 x REE. Nitrogen (N) balance and urinary 3-MeH excretion were determined for the 6 d. In our results, the urine-based estimate of N balance was 22.2 +/- 14.4 (n = 9) mg N.kg-1.d-1 and 60.5 +/- 10.1 mg (n = 8) N.kg-1.d-1 for the control and BCAA-supplemented groups, respectively (P < 0.05). Urinary 3-MeH excretion was unchanged in both groups with bed rest. We conclude that BCAA supplementation attenuates the N loss during short-term bed rest.

Stein, T. P.; Schluter, M. D.; Leskiw, M. J.; Boden, G.

1999-01-01

363

[Serum levels of amino acid in patients with purple urine bag syndrome].  

PubMed

The plastic of urinary catheter drainage bags occasionally turns purple hours or days after catheterization and the color becomes increasingly intense the longer the same drainage system is left in place. This phenomenon was first reported in 1978 as "purple urine bag syndrome", and had been known to occur with bacterial infection of the urinary tract with chronic constipation. Chronic constipation is commonly associated with bacterial overgrowth in the bowel in which tryptophan has been converted to indol and yields the high levels of indigo (blue) and indirubin (red) in urinary bags of patients with bacterial infection of the urine, because indigo-producing bacteria have indoxyl phosphatase or sulfatase that can produce indigo and indirubin. We determined the serum levels of amino acids in patients with purple urine bag syndrome. The serum level of tryptophan and valine were significantly reduced in patients with purple urine bag syndrome. This result suggests that absorption of amino acids was affected by disturbances of colonic motility and intestinal bacterial overgrowth. PMID:9283212

Nakayama, T; Kanmatsuse, K

1997-07-01

364

Direct thin layer chromatography enantioresolution of some basic dl-amino acids using a pharmaceutical industry waste as chiral impregnating reagent  

Microsoft Academic Search

Direct enantiomeric resolution of dl-arginine, dl-histidine, dl-lysine, dl-valine and dl-leucine into their enantiomers was achieved by thin layer chromatography (TLC) on silica gel plates impregnated with optically pure (1R, 3R, 5R)-2-azabicyclo[3,3,0]octan-3-carbo-xylic acid (0.011 M) as a chiral selector which is a waste of a pharmaceutical industry. Different combinations of acetonitrile-methanol-water were found to be successful in resolving the dl-amino acids.

R. Bhushan; J. Martens; G. Thuku Thiongo

2000-01-01

365

The effect of hydrolysis time on amino acid analysis.  

PubMed

Determining the amino acid content of a protein involves the hydrolysis of that protein, usually in acid, until the protein-bound amino acids are released and made available for detection. Both the variability in the ease of peptide bond cleavage and differences in the acid stability of certain amino acids can significantly affect determination of a protein's amino acid content. By using multiple hydrolysis intervals, a greater degree of accuracy can be obtained in amino acid analysis. Correction factors derived by linear extrapolation of serial hydrolysis data are currently used. Compartmental modeling of the simultaneous hydrolysis (yield) and degradation (decay) of amino acids by nonlinear multiple regression of serial hydrolysis data has also been validated and applied to determine the amino acid composition of various biological samples, including egg-white lysozyme, human milk protein, and hair. Implicit in the routine application of serial hydrolysis in amino acid analysis, however, is an understanding that correction factors, derived either linearly or through the more accurate nonlinear multiple regression approach, need to be determined for individual proteins rather than be applied uniformly across all protein types. PMID:16001867

Darragh, Alison J; Moughan, Paul J

2005-01-01

366

Amino Acid Toxicities of Escherichia coli That Are Prevented by Leucyl-tRNA Synthetase Amino Acid Editing  

Microsoft Academic Search

In the first step of protein synthesis, an aminoacyl-tRNA synthetase (aaRSs) is responsible for linking a single standard amino acid to its correct set of tRNA isoacceptors (11, 20). About half of the family of 20 aaRSs are challenged to distin- guish among closely related amino acids and have evolved amino-acid-editing mechanisms to clear their mistakes (10). These editing mechanisms

Vrajesh A. Karkhanis; Anjali P. Mascarenhas; Susan A. Martinis

2007-01-01

367

A Novel meso-Diaminopimelate Dehydrogenase from Symbiobacterium thermophilum: Overexpression, Characterization, and Potential for d-Amino Acid Synthesis  

PubMed Central

meso-Diaminopimelate dehydrogenase (meso-DAPDH) is an NADP+-dependent enzyme which catalyzes the reversible oxidative deamination on the d-configuration of meso-2,6-diaminopimelate to produce l-2-amino-6-oxopimelate. In this study, the gene encoding a meso-diaminopimelate dehydrogenase from Symbiobacterium thermophilum was cloned and expressed in Escherichia coli. In addition to the native substrate meso-2,6-diaminopimelate, the purified enzyme also showed activity toward d-alanine, d-valine, and d-lysine. This enzyme catalyzed the reductive amination of 2-keto acids such as pyruvic acid to generate d-amino acids in up to 99% conversion and 99% enantiomeric excess. Since meso-diaminopimelate dehydrogenases are known to be specific to meso-2,6-diaminopimelate, this is a unique wild-type meso-diaminopimelate dehydrogenase with a more relaxed substrate specificity and potential for d-amino acid synthesis. The enzyme is the most stable meso-diaminopimelate dehydrogenase reported to now. Two amino acid residues (F146 and M152) in the substrate binding sites of S. thermophilum meso-DAPDH different from the sequences of other known meso-DAPDHs were replaced with the conserved amino acids in other meso-DAPDHs, and assay of wild-type and mutant enzyme activities revealed that F146 and M152 are not critical in determining the enzyme's substrate specificity. The high thermostability and relaxed substrate profile of S. thermophilum meso-DAPDH warrant it as an excellent starting enzyme for creating effective d-amino acid dehydrogenases by protein engineering.

Gao, Xiuzhen; Chen, Xi; Liu, Weidong; Feng, Jinhui; Wu, Qiaqing; Hua, Ling

2012-01-01

368

Utilization of Acidic ?-Amino Acids as Acyl Donors: An Effective Stereo-Controllable Synthesis of Aryl-Keto ?-Amino Acids and Their Derivatives.  

PubMed

Aryl-keto-containing ?-amino acids are of great importance in organic chemistry and biochemistry. They are valuable intermediates for the construction of hydroxyl ?-amino acids, nonproteinogenic ?-amino acids, as well as other biofunctional components. Friedel-Crafts acylation is an effective method to prepare aryl-keto derivatives. In this review, we summarize the preparation of aryl-keto containing ?-amino acids by Friedel-Crafts acylation using acidic ?-amino acids as acyl-donors and Lewis acids or Brönsted acids as catalysts. PMID:24840903

Wang, Lei; Murai, Yuta; Yoshida, Takuma; Okamoto, Masashi; Tachrim, Zetryana Puteri; Hashidoko, Yasuyuki; Hashimoto, Makoto

2014-01-01

369

From one amino acid to another: tRNA-dependent amino acid biosynthesis  

PubMed Central

Aminoacyl-tRNAs (aa-tRNAs) are the essential substrates for translation. Most aa-tRNAs are formed by direct aminoacylation of tRNA catalyzed by aminoacyl-tRNA synthetases. However, a smaller number of aa-tRNAs (Asn-tRNA, Gln-tRNA, Cys-tRNA and Sec-tRNA) are made by synthesizing the amino acid on the tRNA by first attaching a non-cognate amino acid to the tRNA, which is then converted to the cognate one catalyzed by tRNA-dependent modifying enzymes. Asn-tRNA or Gln-tRNA formation in most prokaryotes requires amidation of Asp-tRNA or Glu-tRNA by amidotransferases that couple an amidase or an asparaginase to liberate ammonia with a tRNA-dependent kinase. Both archaeal and eukaryotic Sec-tRNA biosynthesis and Cys-tRNA synthesis in methanogens require O-phosophoseryl-tRNA formation. For tRNA-dependent Cys biosynthesis, O-phosphoseryl-tRNA synthetase directly attaches the amino acid to the tRNA which is then converted to Cys by Sep-tRNA: Cys-tRNA synthase. In Sec-tRNA synthesis, O-phosphoseryl-tRNA kinase phosphorylates Ser-tRNA to form the intermediate which is then modified to Sec-tRNA by Sep-tRNA:Sec-tRNA synthase. Complex formation between enzymes in the same pathway may protect the fidelity of protein synthesis. How these tRNA-dependent amino acid biosynthetic routes are integrated into overall metabolism may explain why they are still retained in so many organisms.

Sheppard, Kelly; Yuan, Jing; Hohn, Michael J.; Jester, Brian; Devine, Kevin M.; Soll, Dieter

2008-01-01

370

Supervised learning method for the prediction of subcellular localization of proteins using amino acid and amino acid pair composition  

PubMed Central

Background Occurrence of protein in the cell is an important step in understanding its function. It is highly desirable to predict a protein's subcellular locations automatically from its sequence. Most studied methods for prediction of subcellular localization of proteins are signal peptides, the location by sequence homology, and the correlation between the total amino acid compositions of proteins. Taking amino-acid composition and amino acid pair composition into consideration helps improving the prediction accuracy. Results We constructed a dataset of protein sequences from SWISS-PROT database and segmented them into 12 classes based on their subcellular locations. SVM modules were trained to predict the subcellular location based on amino acid composition and amino acid pair composition. Results were calculated after 10-fold cross validation. Radial Basis Function (RBF) outperformed polynomial and linear kernel functions. Total prediction accuracy reached to 71.8% for amino acid composition and 77.0% for amino acid pair composition. In order to observe the impact of number of subcellular locations we constructed two more datasets of nine and five subcellular locations. Total accuracy was further improved to 79.9% and 85.66%. Conclusions A new SVM based approach is presented based on amino acid and amino acid pair composition. Result shows that data simulation and taking more protein features into consideration improves the accuracy to a great extent. It was also noticed that the data set needs to be crafted to take account of the distribution of data in all the classes.

Habib, Tanwir; Zhang, Chaoyang; Yang, Jack Y; Yang, Mary Qu; Deng, Youping

2008-01-01

371

Amino acids regulate transgene expression in MDCK cells.  

PubMed

Gene expression and cell growth rely on the intracellular concentration of amino acids, which in metazoans depends on extracellular amino acid availability and transmembrane transport. To investigate the impact of extracellular amino acid concentrations on the expression of a concentrative amino acid transporter, we overexpressed the main kidney proximal tubule luminal neutral amino acid transporter B0AT1-collectrin (SLC6A19-TMEM27) in MDCK cell epithelia. Exogenously expressed proteins co-localized at the luminal membrane and mediated neutral amino acid uptake. However, the transgenes were lost over few cell culture passages. In contrast, the expression of a control transgene remained stable. To test whether this loss was due to inappropriately high amino acid uptake, freshly transduced MDCK cell lines were cultivated either with physiological amounts of amino acids or with the high concentration found in standard cell culture media. Expression of exogenous transporters was unaffected by physiological amino acid concentration in the media. Interestingly, mycoplasma infection resulted in a significant increase in transgene expression and correlated with the rapid metabolism of L-arginine. However, L-arginine metabolites were shown to play no role in transgene expression. In contrast, activation of the GCN2 pathway revealed by an increase in eIF2? phosphorylation may trigger transgene derepression. Taken together, high extracellular amino acid concentration provided by cell culture media appears to inhibit the constitutive expression of concentrative amino acid transporters whereas L-arginine depletion by mycoplasma induces the expression of transgenes possibly via stimulation of the GCN2 pathway. PMID:24797296

Torrente, Marta; Guetg, Adriano; Sass, Jörn Oliver; Arps, Lisa; Ruckstuhl, Lisa; Camargo, Simone M R; Verrey, François

2014-01-01

372

Amino Acids Regulate Transgene Expression in MDCK Cells  

PubMed Central

Gene expression and cell growth rely on the intracellular concentration of amino acids, which in metazoans depends on extracellular amino acid availability and transmembrane transport. To investigate the impact of extracellular amino acid concentrations on the expression of a concentrative amino acid transporter, we overexpressed the main kidney proximal tubule luminal neutral amino acid transporter B0AT1-collectrin (SLC6A19-TMEM27) in MDCK cell epithelia. Exogenously expressed proteins co-localized at the luminal membrane and mediated neutral amino acid uptake. However, the transgenes were lost over few cell culture passages. In contrast, the expression of a control transgene remained stable. To test whether this loss was due to inappropriately high amino acid uptake, freshly transduced MDCK cell lines were cultivated either with physiological amounts of amino acids or with the high concentration found in standard cell culture media. Expression of exogenous transporters was unaffected by physiological amino acid concentration in the media. Interestingly, mycoplasma infection resulted in a significant increase in transgene expression and correlated with the rapid metabolism of L-arginine. However, L-arginine metabolites were shown to play no role in transgene expression. In contrast, activation of the GCN2 pathway revealed by an increase in eIF2? phosphorylation may trigger transgene derepression. Taken together, high extracellular amino acid concentration provided by cell culture media appears to inhibit the constitutive expression of concentrative amino acid transporters whereas L-arginine depletion by mycoplasma induces the expression of transgenes possibly via stimulation of the GCN2 pathway.

Torrente, Marta; Guetg, Adriano; Sass, Jorn Oliver; Arps, Lisa; Ruckstuhl, Lisa; Camargo, Simone M. R.; Verrey, Francois

2014-01-01

373

Gas-phase Acidities of Aspartic Acid, Glutamic Acid, and their Amino Acid Amides.  

SciTech Connect

Gas-phase acidities (GA or ?Gacid) for the two most acidic common amino acids, aspartic acid and glutamic acid, have been determined for the first time. Because of the amide linkage’s importance in peptides and as an aid in studying side chain versus main chain deprotonation, aspartic acid amide and glutamic acid amide were also studied. Experimental GA values were measured by proton transfer reactions in an electrospray ionization/Fourier transform ion cyclotron resonance mass spectrometer. Calculated GAs were obtained by density functional and molecular orbital theory approaches. The best agreement with experiment was found at the G3MP2 level; the MP2/CBS and B3LYP/aug-cc-pVDZ results are 3–4 kcal/mol more acidic than the G3MP2 results. Experiment shows that aspartic acid is more acidic than glutamic acid by ca. 3 kcal/mol whereas the G3MP2 results show a smaller acidity difference of 0.2 kcal/mol. Similarly, aspartic acid amide is experimentally observed to be ca. 2 kcal/mol more acidic than glutamic acid amide whereas the G3MP2 results show a correspondingly smaller energy difference of 0.7 kcal/mol. The computational results clearly show that the anions are all ring-like structures with strong hydrogen bonds between the OH or NH2 groups and the CO2? group from which the proton is removed. The two amino acids are main-chain deprotonated. In addition, use of the COSMO model for the prediction of the free energy differences in aqueous solution gave values in excellent agreement with the most recent experimental values for pKa. Glutamic acid is predicted to be more acidic than aspartic acid in aqueous solution due to differential solvation effects.

Li, Zhong; Matus, Myrna H.; Velazquez, Hector A.; Dixon, David A.; Cassady, Carolyn J.

2007-02-14

374

Gas-phase acidities of aspartic acid, glutamic acid, and their amino acid amides  

NASA Astrophysics Data System (ADS)

Gas-phase acidities (GA or [Delta]Gacid) for the two most acidic common amino acids, aspartic acid and glutamic acid, have been determined for the first time. Because of the amide linkage's importance in peptides and as an aid in studying side chain versus main chain deprotonation, aspartic acid amide and glutamic acid amide were also studied. Experimental GA values were measured by proton transfer reactions in an electrospray ionization/Fourier transform ion cyclotron resonance mass spectrometer. Calculated GAs were obtained by density functional and molecular orbital theory approaches. The best agreement with experiment was found at the G3MP2 level; the MP2/CBS and B3LYP/aug-cc-pVDZ results are 3-4 kcal/mol more acidic than the G3MP2 results. Experiment shows that aspartic acid is more acidic than glutamic acid by ca. 3 kcal/mol whereas the G3MP2 results show a smaller acidity difference of 0.2 kcal/mol. Similarly, aspartic acid amide is experimentally observed to be ca. 2 kcal/mol more acidic than glutamic acid amide whereas the G3MP2 results show a correspondingly smaller energy difference of 0.7 kcal/mol. The computational results clearly show that the anions are all ring-like structures with strong hydrogen bonds between the OH or NH2 groups and the CO2- group from which the proton is removed. The two amino acids are main-chain deprotonated. In addition, use of the COSMO model for the prediction of the free energy differences in aqueous solution gave values in excellent agreement with the most recent experimental values for pKa. Glutamic acid is predicted to be more acidic than aspartic acid in aqueous solution due to differential solvation effects.

Li, Zhong; Matus, Myrna H.; Velazquez, Hector Adam; Dixon, David A.; Cassady, Carolyn J.

2007-09-01

375

Site specific incorporation of keto amino acids into proteins  

DOEpatents

Compositions and methods of producing components of protein biosynthetic machinery that include orthogonal tRNAs, orthogonal aminoacyl-tRNA synthetases, and orthogonal pairs of tRNAs/synthetases, which incorporate keto amino acids into proteins are provided. Methods for identifying these orthogonal pairs are also provided along with methods of producing proteins with keto amino acids using these orthogonal pairs.

Schultz, Peter G. (La Jolla, CA); Wang, Lei (San Diego, CA)

2009-04-28

376

Production of amino acids using auxotrophic mutants of methylotrophic bacillus  

DOEpatents

A method of producing amino acids by culturing an amino acid auxotroph of a biologically pure strain of a type I methylotrophic bacterium of the genus Bacillus which exhibits sustained growth at 50.degree. C. using methanol as a carbon and energy source and requiring vitamin B.sub.12 and biotin is provided.

Hanson, Richard S. (Wayzata, MN); Flickinger, Michael C. (St. Paul, MN); Schendel, Frederick J. (Falcon Heights, MN); Guettler, Michael V. (Waconia, MN)

2001-07-17

377

Molecular regulation of amino acid biosynthesis in plants  

Microsoft Academic Search

Our understanding of amino acid biosynthesis in plants has grown by leaps and bounds in the last decade. It appears that most of the amino acid biosynthesis takes place in the chloroplast. Recent demonstration of glutamine synthetase and DAHP synthase in the vascular tisuue has added a new dimension in the complexity of the nitrogen cycle in plants. Isolation of

B. K. Singh; B. F. Matthews

1994-01-01

378

Amino Acid Difference Formula to Help Explain Protein Evolution  

Microsoft Academic Search

A formula for difference between amino acids combines properties that correlate best with protein residue substitution frequencies: composition, polarity, and molecular volume. Substitution frequencies agree much better with overall chemical difference between exchanging residues than with minimum base changes between their codons. Correlation coefficients show that fixation of mutations between dissimilar amino acids is generally rare.

R. Grantham

1974-01-01

379

Modeling amino acid substitution patterns in orthologous and paralogous genes  

Microsoft Academic Search

We study to what degree patterns of amino acid substitution vary between genes using two models of protein-coding gene evolution. The first divides the amino acids into groups, with one substitution rate for pairs of residues in the same group and a second for those in differing groups. Unlike previous applications of this model, the groups themselves are estimated from

Gavin C. Conant; Günter P. Wagner; Peter F. Stadler

2007-01-01

380

Site specific incorporation of keto amino acids into proteins  

DOEpatents

Compositions and methods of producing components of protein biosynthetic machinery that include orthogonal tRNAs, orthogonal aminoacyl-tRNA synthetases, and orthogonal pairs of tRNAs/synthetases, which incorporate keto amino acids into proteins are provided. Methods for identifying these orthogonal pairs are also provided along with methods of producing proteins with keto amino acids using these orthogonal pairs.

Schultz, Peter G. (La Jolla, CA); Wang, Lei (San Diego, CA)

2011-12-06

381

Site specific incorporation of keto amino acids into proteins  

DOEpatents

Compositions and methods of producing components of protein biosynthetic machinery that include orthogonal tRNAs, orthogonal aminoacyl-tRNA synthetases, and orthogonal pairs of tRNAs/synthetases, which incorporate keto amino acids into proteins are provided. Methods for identifying these orthogonal pairs are also provided along with methods of producing proteins with keto amino acids using these orthogonal pairs.

Schultz, Peter G. (La Jolla, CA); Wang, Lei (San Diego, CA)

2011-03-22

382

Site specific incorporation of keto amino acids into proteins  

DOEpatents

Compositions and methods of producing components of protein biosynthetic machinery that include orthogonal tRNAs, orthogonal aminoacyl-tRNA synthetases, and orthogonal pairs of tRNAs/synthetases, which incorporate keto amino acids into proteins are provided. Methods for identifying these orthogonal pairs are also provided along with methods of producing proteins with keto amino acids using these orthogonal pairs.

Schultz, Peter G. (La Jolla, CA); Wang, Lei (San Diego, CA)

2012-02-14

383

Amino Acid Diets and Maximal Growth in the Rat  

Microsoft Academic Search

Amino acid diets fed in an agar gel have been found to support weight gains of rats as great or greater than those obtained with diets containing an equiva lent quantity of casein supplemented with methionine. Over 1% arginine, 0.6% asparagine and feeding the diet in gel form were necessary to obtain maximal weight gain. The diet contained amino acids

Q. R. ROGERS ANDA; E. HARPER

384

Amino acid metabolism and the energetics of growth  

Microsoft Academic Search

The nonessential amino acids are involved in a large number of functions that are not directly associated with protein synthesis. Recent studies using a combination of transorgan balance and stable isotopic tracers have demonstrated that a substantial portion of the extra?splanchnic flux of glutamate, glutamine, glycine and cysteine derives from tissue synthesis. A key amino acid in this respect is

P. J. Reeds; D. G. Burrin; T. A. Davis; B. Stoll

1998-01-01

385

Targets of Amino Acid Restriction in Prostate Cancer  

Cancer.gov

The objective of this application is to identify the molecular target(s) by which specific amino acid dependency modulates the viability and invasiveness of human androgen-independent prostate cancer calls. We hypothesize that specific amino acid-regulated invasion is dependent on the inhibition of FAK and its binding partners.

386

Plasma Amino Acid Response to Graded Levels of Escape Protein  

Microsoft Academic Search

A trial was conducted to examine the potential of using plasma amino acid responses to graded levels of escape protein to determine limiting amino acids in cattle. Growing calves (n = 120; i BW = 220 f 21 kg) were fed a basal diet of corncobsorghum silage (61:39) and were individually supplemented with distillers' dried grains (DDG), heat-damaged DDG (H-DDG),

D. J. Gibb; T. J. Klopfenstein; R. A. Britton; A. J. Lewis

2010-01-01

387

Stability of free amino acid levels in stressed Abarenicola pacifica  

Microsoft Academic Search

JEFFRIES (1972), BAYNE et al. (1976), and ROESIJADI + ANDERSON (1979) have described a change in the composition of the free amino acid (FAA) pool of pelecypod molluscs under stress. This response consists of a significant decrease in the level of glycine, while the taurine level remains constant, leading to a decrease in the total free amino acid level and

J. M. Augenfeld; J. W. Anderson

1980-01-01

388

Two types of amino acid substitutions in protein evolution  

Microsoft Academic Search

Summary The frequency of amino acid substitutions, relative to the frequency expected by chance, decreases linearly with the increase in physico-chemical differences between amino acid pairs involved in a substitution. This correlation does not apply to abnormal human hemoglobins. Since abnormal hemoglobins mostly reflect the process of mutation rather than selection, the correlation manifest during protein evolution between substitution frequency

Takashi Miyata; Sanzo Miyazawa; Teruo Yasunaga

1979-01-01

389

Amino Acids in Uremia. Short-Term Daily Peritoneal Dialysis.  

National Technical Information Service (NTIS)

The research has been directed toward the study: (1) of adverse effects among basic amino-acids in uremia, (2) of short daily peritoneal dialysis. Small amino acid loads have been administered orally to a group of normal and uremic subjects. Fasting plasm...

C. Giordano N. G. De Santo E. Esposito

1974-01-01

390

The amino acid sequence of snapping turtle (Chelydra serpentina) ribonuclease  

Microsoft Academic Search

Snapping turtle (Chelydra serpentina) ribonuclease was isolated from pancreatic tissue. Turtle ribonuclease binds much more weakly to the affinity chromatography matrix used than mammalian ribonucleases. The amino acid sequence was determined from overlapping peptides obtained from three different digests. The N-terminal amino acid sequence of the protein determined by others and homology were used as additional evidence for several overlaps.

Cornelis Schüller; Jaap J. Beintema; Jaap Broos; Janneke Meulenberg

1985-01-01

391

Amino acids from ultraviolet irradiation of interstellar ice analogues  

Microsoft Academic Search

Amino acids are the essential molecular components of living organisms on Earth, but the proposed mechanisms for their spontaneous generation have been unable to account for their presence in Earth's early history. The delivery of extraterrestrial organic compounds has been proposed as an alternative to generation on Earth, and some amino acids have been found in several meteorites. Here we

G. M. Muñoz Caro; U. J. Meierhenrich; W. A. Schutte; B. Barbier; A. Arcones Segovia; H. Rosenbauer; W. H.-P. Thiemann; A. Brack; J. M. Greenberg

2002-01-01

392

Urinary amino acid analysis: a comparison of iTRAQ-LC-MS/MS, GC-MS, and amino acid analyzer.  

PubMed

Urinary amino acid analysis is typically done by cation-exchange chromatography followed by post-column derivatization with ninhydrin and UV detection. This method lacks throughput and specificity. Two recently introduced stable isotope ratio mass spectrometric methods promise to overcome those shortcomings. Using two blinded sets of urine replicates and a certified amino acid standard, we compared the precision and accuracy of gas chromatography/mass spectrometry (GC-MS) and liquid chromatography-tandem mass spectrometry (LC-MS/MS) of propyl chloroformate and iTRAQ derivatized amino acids, respectively, to conventional amino acid analysis. The GC-MS method builds on the direct derivatization of amino acids in diluted urine with propyl chloroformate, GC separation and mass spectrometric quantification of derivatives using stable isotope labeled standards. The LC-MS/MS method requires prior urinary protein precipitation followed by labeling of urinary and standard amino acids with iTRAQ tags containing different cleavable reporter ions distinguishable by MS/MS fragmentation. Means and standard deviations of percent technical error (%TE) computed for 20 amino acids determined by amino acid analyzer, GC-MS, and iTRAQ-LC-MS/MS analyses of 33 duplicate and triplicate urine specimens were 7.27+/-5.22, 21.18+/-10.94, and 18.34+/-14.67, respectively. Corresponding values for 13 amino acids determined in a second batch of 144 urine specimens measured in duplicate or triplicate were 8.39+/-5.35, 6.23+/-3.84, and 35.37+/-29.42. Both GC-MS and iTRAQ-LC-MS/MS are suited for high-throughput amino acid analysis, with the former offering at present higher reproducibility and completely automated sample pretreatment, while the latter covers more amino acids and related amines. PMID:19481989

Kaspar, Hannelore; Dettmer, Katja; Chan, Queenie; Daniels, Scott; Nimkar, Subodh; Daviglus, Martha L; Stamler, Jeremiah; Elliott, Paul; Oefner, Peter J

2009-07-01

393

Net placental transfer of free amino acids against varying concentrations  

PubMed Central

1. The patterns of the free plasma amino acids in the pregnant guinea-pig and her foetuses, near term, are described. The concentration of each amino acid was higher in the foetal plasma than in the maternal. The foetal:maternal gradients (F:M) varied for each amino acid; the straight chain amino acids had the highest F:M ratios. 2. Net transfer of endogenous plasma amino acids, from the maternal circulation across the placental membrane, was studied. The foetus was removed and the foetal placenta perfused in situ via the umbilical arteries, with an artificial fluid containing varying concentrations of amino acids. 3. All the amino acids, both essential and non-essential, could be transferred from the maternal to the foetal circulation against the F:M gradients. With `closed circuit' perfusion, this transport increased the concentration of total amino N in the perfusate until it was twice that of the normal F:M gradient of 5. The concentrations of the individual amino acids was increased to 1·7-4·2 times those normally present in foetal plasma, and the final values reached were similar to the concentrations of free amino acid found in placental tissue. 4. The umbilical vein—artery differences were small, with the placenta perfused `open circuit' in the steady state, using physiological flow rates and amino acid concentrations. The average net placental transfer of amino N found was 1·14 m-mole min-1. This is about 60% of the calculated net rate of accumulation of N by the 60 g guinea-pig foetus. 5. The influence of foetal placental perfusion concentration on transfer was small but significant. In the steady state, the transfer of amino N, and each individual amino acid, was found to be inversely proportional to the concentrations in the perfusate when the placenta was perfused `open circuit'. The slopes of the regression of transfer on concentration had an average value of 0·13 n-mole min-1 g-1 per ?mole. No significant difference in the slopes was found between the three amino acid transport groups. 6. Net transfer was independent of perfusate flow, within the physiological range, which suggests a secretory process across the membrane from maternal to foetal circulation.

Hill, Penny M. M.; Young, Maureen

1973-01-01

394

Amino acids and osmolarity in honeybee drone haemolymph.  

PubMed

In the haemolymph of honeybee drones, concentrations of free amino acids were higher than in worker haemolymph, with different relative proportions of individual amino acids. The overall concentration of free amino acids reached its highest level at the 5th day after adult drone emergence, and after the 9th day only minor changes in the concentration and distribution of free amino acids were observed. This coincides with the age when drones reach sexual maturity and change their feeding behaviour. Levels of essential free amino acids were high during the first 3 days of life and thereafter decreased. Osmolarity was lowest at emergence (334 +/- 42 mOsm), increased until the age of 3 days (423 +/- 32 mOsm) and then stayed generally constant until the 16th day of life. Only 25-day-old drones had significantly higher osmolarity (532 +/- 38 mOsm). The overall change in osmolarity during a drone's lifetime was about 40%. PMID:10524277

Leonhard, B; Crailsheim, K

1999-01-01

395

Stardust, Supernovae and the Chirality of the Amino Acids  

SciTech Connect

A mechanism for creating enantiomerism in the amino acids, the building blocks of the proteins, that involves global selection of one chirality by interactions between the amino acids and neutrinos from core-collapse supernovae is described. The selection involves the dependence of the interaction cross sections on the orientations of the spins of the neutrinos and the 14N nuclei in the amino acids, or in precursor molecules, which in turn couple to the molecular chirality. The subsequent chemical evolution and galactic mixing would ultimately populate the Galaxy with the selected species. The resulting amino acids could either be the source thereof on Earth, or could have triggered the chirality that was ultimately achieved for Earth's amino acids.

Boyd, R N; Kajino, T; Onaka, T

2011-03-09

396

A mathematical model for the branched chain amino acid biosynthetic pathways of Escherichia coli K12.  

PubMed

As a first step toward the elucidation of the systems biology of the model organism Escherichia coli, it was our goal to mathematically model a metabolic system of intermediate complexity, namely the well studied end product-regulated pathways for the biosynthesis of the branched chain amino acids L-isoleucine, L-valine, and L-leucine. This has been accomplished with the use of kMech (Yang, C.-R., Shapiro, B. E., Mjolsness, E. D., and Hatfield, G. W. (2005) Bioinformatics 21, in press), a Cellerator (Shapiro, B. E., Levchenko, A., Meyerowitz, E. M., Wold, B. J., and Mjolsness, E. D. (2003) Bioinformatics 19, 677-678) language extension that describes a suite of enzyme reaction mechanisms. Each enzyme mechanism is parsed by kMech into a set of fundamental association-dissociation reactions that are translated by Cellerator into ordinary differential equations. These ordinary differential equations are numerically solved by Mathematica. Any metabolic pathway can be simulated by stringing together appropriate kMech models and providing the physical and kinetic parameters for each enzyme in the pathway. Writing differential equations is not required. The mathematical model of branched chain amino acid biosynthesis in E. coli K12 presented here incorporates all of the forward and reverse enzyme reactions and regulatory circuits of the branched chain amino acid biosynthetic pathways, including single and multiple substrate (Ping Pong and Bi Bi) enzyme kinetic reactions, feedback inhibition (allosteric, competitive, and non-competitive) mechanisms, the channeling of metabolic flow through isozymes, the channeling of metabolic flow via transamination reactions, and active transport mechanisms. This model simulates the results of experimental measurements. PMID:15657047

Yang, Chin-Rang; Shapiro, Bruce E; Hung, She-Pin; Mjolsness, Eric D; Hatfield, G Wesley

2005-03-25

397

Amino Acid Analyses of Acid Hydrolysates in Desert Varnish  

NASA Technical Reports Server (NTRS)

There has long been a debate as to whether rock varnish deposits are microbially mediated or are deposited by inorganic processes. Varnished rocks are found throughout the world primarily in arid and semi-arid regions. The varnish coats are typically up to 200 microns thick and are composed of clays and alternating layers enriched in manganese and iron oxides. The individual layers range in thickness from 1 micron to greater than 10 microns and may continue laterally for more than a 100 microns. Overlapping botryoidal structures are visible in thin section and scanning electron micrographs. The coatings also include small amounts of organic mater and detrital grains. Amino-acid hydrolysates offer a means of assessing the organic composition of rock varnish collected from the Sonoran Desert, near Phoenix, AZ. Chromatographic analyses of hydrolysates from powdered samples of rock varnish suggest that the interior of rock varnish is relatively enriched in amino acids and specifically in d-alanine and glutamic acid. Peptidoglycan (murein) is the main structural component of gram-positive bacterial cell walls. The d-enantiomer of alanine and glutamic acid are specific to peptidoglycan and are consequently an indicator for the presence of bacteria. D-alanine is also found in teichoic acid which is only found in gram-positive bacteria. Several researchers have cultured bacteria from the surface of rock varnish and most have been gram-positive, suggesting that gram-positive bacteria are intimately associated with varnish coatings and may play a role in the formation of varnish coatings.

Perry, Randall S.; Staley, James T.; Dworkin,