Valine (symbol Val or V) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain isopropyl group, making it a non-polar aliphatic amino acid. Valine is essential in humans, meaning the body cannot synthesize it; it must be obtained from dietary sources which are foods that contain proteins, such as meats, dairy products, soy products, beans and legumes. It is encoded by all codons starting with GU (GUU, GUC, GUA, and GUG). |
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InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1 |
KZSNJWFQEVHDMF-BYPYZUCNSA-N |
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
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PubMed
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Chlamydomonas reinhardtii
(NCBI:txid3055)
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See:
PubMed
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Saccharomyces cerevisiae
(NCBI:txid4932)
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Source: yeast.sf.net
See:
PubMed
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Escherichia coli
(NCBI:txid562)
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See:
PubMed
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Homo sapiens
(NCBI:txid9606)
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See:
DOI
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Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
micronutrient
Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via valine )
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
(via valine )
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nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
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View more via ChEBI Ontology
(2S)-2-amino-3-methylbutanoic acid
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IUPAC
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(S)-valine
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ChemIDplus
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2-Amino-3-methylbutyric acid
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KEGG COMPOUND
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L-(+)-alpha-Aminoisovaleric acid
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HMDB
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L-alpha-Amino-beta-methylbutyric acid
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HMDB
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L-Valin
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ChEBI
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L-Valine
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KEGG COMPOUND
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V
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ChEBI
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Val
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ChEBI
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VALINE
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PDBeChem
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4128
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DrugCentral
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C00001398
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KNApSAcK
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C00183
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KEGG COMPOUND
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D00039
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KEGG DRUG
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DB00161
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DrugBank
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HMDB0000883
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HMDB
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L-valine
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Wikipedia
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VAL
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MetaCyc
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VAL
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PDBeChem
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View more database links |
1721136
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Reaxys Registry Number
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Reaxys
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2827
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Gmelin Registry Number
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Gmelin
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72-18-4
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CAS Registry Number
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KEGG COMPOUND
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72-18-4
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CAS Registry Number
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ChemIDplus
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72-18-4
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CAS Registry Number
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NIST Chemistry WebBook
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Hasegawa S, Uematsu K, Natsuma Y, Suda M, Hiraga K, Jojima T, Inui M, Yukawa H (2012) Improvement of the redox balance increases L-valine production by Corynebacterium glutamicum under oxygen deprivation conditions. Applied and environmental microbiology 78, 865-875 [PubMed:22138982] [show Abstract] Production of L-valine under oxygen deprivation conditions by Corynebacterium glutamicum lacking the lactate dehydrogenase gene ldhA and overexpressing the L-valine biosynthesis genes ilvBNCDE was repressed. This was attributed to imbalanced cofactor production and consumption in the overall L-valine synthesis pathway: two moles of NADH was generated and two moles of NADPH was consumed per mole of L-valine produced from one mole of glucose. In order to solve this cofactor imbalance, the coenzyme requirement for L-valine synthesis was converted from NADPH to NADH via modification of acetohydroxy acid isomeroreductase encoded by ilvC and introduction of Lysinibacillus sphaericus leucine dehydrogenase in place of endogenous transaminase B, encoded by ilvE. The intracellular NADH/NAD(+) ratio significantly decreased, and glucose consumption and L-valine production drastically improved. Moreover, L-valine yield increased and succinate formation decreased concomitantly with the decreased intracellular redox state. These observations suggest that the intracellular NADH/NAD(+) ratio, i.e., reoxidation of NADH, is the primary rate-limiting factor for L-valine production under oxygen deprivation conditions. The L-valine productivity and yield were even better and by-products derived from pyruvate further decreased as a result of a feedback resistance-inducing mutation in the acetohydroxy acid synthase encoded by ilvBN. The resultant strain produced 1,470 mM L-valine after 24 h with a yield of 0.63 mol mol of glucose(-1), and the L-valine productivity reached 1,940 mM after 48 h. | Waguespack AM, Bidner TD, Payne RL, Southern LL (2012) Valine and isoleucine requirement of 20- to 45-kilogram pigs. Journal of animal science 90, 2276-2284 [PubMed:22287678] [show Abstract] Three experiments were conducted to determine the Val and Ile requirements in low-CP, corn-soybean meal (C-SBM) AA-supplemented diets for 20- to 45-kg pigs. All experiments were conducted for 26 to 27 d with purebred or crossbred barrows and gilts, which were blocked by initial BW. Treatments were replicated with 5 or 6 pens of 3 or 4 pigs per pen. At the beginning of Exp. 1 and the end of all experiments, blood samples were obtained from all pigs to determine plasma urea N (PUN) concentrations. All diets were C-SBM with 0.335% supplemental Lys to achieve 0.83% standardized ileal digestible (SID) Lys, which is the Lys requirement of these pigs. In Exp. 1, 0, 0.02, 0.04, 0.06, 0.08, or 0.10% L-Val was supplemented to achieve 0.51, 0.53, 0.55, 0.57, 0.59, or 0.61% dietary SID Val, and Thr, Trp, Met, and Ile were supplemented to maintain Thr:Lys, Trp:Lys, TSAA:Lys, and Ile:Lys ratios of 0.71, 0.20, 0.62, and 0.60, respectively. Also, supplemental Gly and Glu were added to all diets to achieve 1.66% Gly + Ser and 3.28% Glu, which is equal to the Gly + Ser and Glu content of a previously validated positive control diet that contained no supplemental AA. Treatment differences were considered significant at P < 0.10. Valine addition increased ADG, ADFI, and G:F in pigs fed 0.51 to 0.59% SID Val (linear, P < 0.08), but ADG and ADFI were decreased at 0.61% SID Val (quadratic, P ≤ 0.10). On the basis of ADG and G:F, the SID Val requirement is between 0.56 and 0.58% in a C-SBM diet supplemented with AA. In Exp. 2 and 3, 0, 0.02, 0.04, 0.06, or 0.08% L-Ile was supplemented to achieve 0.43, 0.45, 0.47, 0.49, or 0.51% dietary SID Ile, and Thr, Trp, Met, and Ile were supplemented to maintain Thr:Lys, Trp:Lys, TSAA:Lys, and Val:Lys ratios of 0.71, 0.20, 0.62, and 0.74, respectively. Also, supplemental Gly and Glu were added to achieve 1.66% Gly + Ser and 3.28% Glu as in Exp. 1. Data from Exp. 2 and 3 were combined and analyzed as 1 data set. Daily BW gain, ADFI, and G:F were not affected by Ile additions to the diet; however, ADFI was decreased among pigs fed the diet with 0.45% SID Ile (P < 0.10) compared with pigs fed the 0.43% SID Ile diet. Broken-line analysis requirements could not be estimated for the combined data from Exp. 2 or 3. The results of this research indicate that the SID Val requirement is between 0.56 to 0.58% (0.67 to 0.70 SID Val:Lys), and the Ile requirement is adequate at 0.43% SID Ile (0.52 SID Ile:Lys) for 20- to 45-kg pigs. | Gloaguen M, Le Floc'h N, Corrent E, Primot Y, van Milgen J (2012) 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 α-keto acid concentrations in pigs. Journal of animal science 90, 3135-3142 [PubMed:22585822] [show Abstract] 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 α-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. | Hou X, Ge X, Wu D, Qian H, Zhang W (2012) Improvement of L-valine production at high temperature in Brevibacterium flavum by overexpressing ilvEBNrC genes. Journal of industrial microbiology & biotechnology 39, 63-72 [PubMed:21706252] [show Abstract] Brevibacterium flavum ATCC14067 was engineered for L: -valine production by overexpression of different ilv genes; the ilvEBN(r)C genes from B. flavum NV128 provided the best candidate for L: -valine production. In traditional fermentation, L: -valine production reached 30.08 ± 0.92 g/L at 31°C in 72 h with a low conversion efficiency of 0.129 g/g. To further improve the L: -valine production and conversion efficiency based on the optimum temperatures of L: -valine biosynthesis enzymes (above 35°C) and the thermotolerance of B. flavum, the fermentation temperature was increased to 34, 37, and 40°C. As a result, higher metabolic rate and L: -valine biosynthesis enzymes activity were obtained at high temperature, and the maximum L: -valine production, conversion efficiency, and specific L: -valine production rate reached 38.08 ± 1.32 g/L, 0.241 g/g, and 0.133 g g(-1) h(-1), respectively, at 37°C in 48 h fermentation. The strategy for enhancing L: -valine production by overexpression of key enzymes in thermotolerant strains may provide an alternative approach to enhance branched-chain amino acids production with other strains. | Arguello-Astorga G, Ascencio-Ibáñez JT, Dallas MB, Orozco BM, Hanley-Bowdoin L (2007) High-frequency reversion of geminivirus replication protein mutants during infection. Journal of virology 81, 11005-11015 [PubMed:17670823] [show Abstract] The geminivirus replication protein AL1 interacts with retinoblastoma-related protein (RBR), a key regulator of the plant division cell cycle, to induce conditions permissive for viral DNA replication. Previous studies of tomato golden mosaic virus (TGMV) AL1 showed that amino acid L148 in the conserved helix 4 motif is critical for RBR binding. In this work, we examined the effect of an L148V mutation on TGMV replication in tobacco cells and during infection of Nicotiana benthamiana plants. The L148V mutant replicated 100 times less efficiently than wild-type TGMV in protoplasts but produced severe symptoms that were delayed compared to those of wild-type infection in plants. Analysis of progeny viruses revealed that the L148V mutation reverted at 100% frequency in planta to methionine, leucine, isoleucine, or a second-site mutation depending on the valine codon in the initial DNA sequence. Similar results were seen with another geminivirus, cabbage leaf curl virus (CaLCuV), carrying an L145A mutation in the equivalent residue. Valine was the predominant amino acid recovered from N. benthamiana plants inoculated with the CaLCuV L145A mutant, while threonine was the major residue in Arabidopsis thaliana plants. Together, these data demonstrated that there is strong selection for reversion of the TGMV L148V and CaLCuV L145A mutations but that the nature of the selected revertants is influenced by both the viral background and host components. These data also suggested that high mutation rates contribute to the rapid evolution of geminivirus genomes in plants. | Riazi R, Rafii M, Wykes LJ, Ball RO, Pencharz PB (2003) Valine may be the first limiting branched-chain amino acid in egg protein in men. The Journal of nutrition 133, 3533-3539 [PubMed:14608070] [show Abstract] Recently, we defined an estimate for total branched-chain amino acids (BCAA) using the indicator amino acid oxidation technique in men fed the three BCAA (leucine, isoleucine and valine) in the proportion present in egg protein. Although egg protein is regarded as a high quality dietary protein source, it is not known whether the proportions of the three BCAA are optimal. Five men with known total BCAA requirements were restudied. Each men was studied with isoleucine, leucine or valine held constant at that individual's requirement level while the intake of the other two BCAA was reduced; one BCAA was held constant and the intake of the other two was reduced by 10 and 20% in random order. The label appearance from the oxidation of L-[13C]-phenylalanine to 13CO2 (F13CO2) in breath was monitored in response to the change in amino acid intake. When either isoleucine or leucine was held constant, and the other two BCAA reduced by 20% (valine and leucine, or valine and isoleucine, respectively) F13CO2 increased (P = 0.007, P = 0.038, respectively). We conclude that valine may be the first limiting BCAA in egg protein. |
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