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Identification
YMDB IDYMDB00152
NameL-Valine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionValine (abbreviated as Val or V) is an alpha-amino acid. The L-isomer is one of the 22 proteinogenic amino acids, i.e., the building blocks of proteins. It is classified as a nonpolar branched chain amino acid, because of the hydrophobic nature of its branched alkyl side chain. S. cerevisiae degrade the branched-chain amino acids (valine, leucine, and iso-leucine) via the Ehrlich pathway. This pathway consists of 3 steps: 1) deamination of the amino acid to the corresponding alpha-keto acid; 2) decarboxylation of the resulting alpha-keto acid to the respective aldehyde; and, 3) reduction of the aldehyde to form the corresponding long chain or complex alcohol, known as a fusel alcohol or fusel oil. Fusel alcohols are important flavor and aroma compounds in yeast-fermented food products and beverages. Each of the three steps in branched-chain amino acid degradation can be catalyzed by more than one isozyme; which enzyme is used appears to depend on the amino acid, the carbon source and the stage of growth of the culture.
Structure
Thumb
Synonyms
  • (2S)-2-Amino-3-methylbutanoate
  • (2S)-2-Amino-3-methylbutanoic acid
  • (S)-2-amino-3-methyl-Butanoate
  • (S)-2-amino-3-methyl-Butanoic acid
  • (S)-2-Amino-3-methylbutanoate
  • (S)-2-Amino-3-methylbutanoic acid
  • (S)-2-Amino-3-methylbutyrate
  • (S)-2-Amino-3-methylbutyric acid
  • (S)-a-Amino-b-methylbutyrate
  • (S)-a-Amino-b-methylbutyric acid
  • (S)-alpha-Amino-beta-methylbutyrate
  • (S)-alpha-Amino-beta-methylbutyric acid
  • (S)-Valine
  • 2-Amino-3-methylbutanoate
  • 2-Amino-3-methylbutanoic acid
  • 2-Amino-3-methylbutyrate
  • 2-Amino-3-methylbutyric acid
  • L-(+)-a-Aminoisovalerate
  • L-(+)-a-Aminoisovaleric acid
  • L-(+)-alpha-Aminoisovalerate
  • L-(+)-alpha-Aminoisovaleric acid
  • L-a-Amino-b-methylbutyrate
  • L-a-Amino-b-methylbutyric acid
  • L-alpha-Amino-beta-methylbutyrate
  • L-alpha-Amino-beta-methylbutyric acid
  • L-valine
  • valine
  • L-Valin
  • V
  • Val
  • L-(+)-Α-aminoisovalerate
  • L-(+)-Α-aminoisovaleric acid
  • L-Α-amino-β-methylbutyrate
  • L-Α-amino-β-methylbutyric acid
  • L Valine
CAS number72-18-4
WeightAverage: 117.1463
Monoisotopic: 117.078978601
InChI KeyKZSNJWFQEVHDMF-BYPYZUCNSA-N
InChIInChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1
IUPAC Name(2S)-2-amino-3-methylbutanoic acid
Traditional IUPAC NameL-valine
Chemical FormulaC5H11NO2
SMILES[H]OC(=O)[C@@]([H])(N([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentValine and derivatives
Alternative Parents
Substituents
  • Valine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point295-300 °C
Experimental Properties
PropertyValueReference
Water Solubility58.5 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-2.26 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility214 g/LALOGPS
logP-2.3ALOGPS
logP-2ChemAxon
logS0.26ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)9.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.49 m³·mol⁻¹ChemAxon
Polarizability12.19 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
OdorlessFDB012740
SMPDB Pathways
Pantothenate and CoA biosynthesisPW002463 ThumbThumb?image type=greyscaleThumb?image type=simple
Valine BiosynthesisPW002474 ThumbThumb?image type=greyscaleThumb?image type=simple
Valine DegradationPW002489 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Pantothenate and CoA biosynthesisec00770 Map00770
Propanoate metabolismec00640 Map00640
Valine, leucine and isoleucine biosynthesisec00290 Map00290
Valine, leucine and isoleucine degradationec00280 Map00280
SMPDB Reactions
L-Valine + Pyruvic acidL-Alanine + Alpha-Ketoisovaleric acid
Alpha-Ketoisovaleric acid + L-Glutamic acidOxoglutaric acid + L-Valine
3-Methylbutanoic acid + L-Glutamic acidOxoglutaric acid + L-Valine
L-Valine + Oxoglutaric acidL-Glutamic acid + Alpha-Ketoisovaleric acid
L-Valine + Oxoglutaric acidL-Glutamic acid + Alpha-Ketoisovaleric acid
KEGG Reactions
Oxoglutaric acid + L-ValineL-Glutamic acid + Alpha-Ketoisovaleric acid
Oxoglutaric acid + L-ValineL-Glutamic acid + Alpha-Ketoisovaleric acid
Adenosine triphosphate + L-Valine + tRNA(Val) → Adenosine monophosphate + Pyrophosphate + Val-tRNA(Val)
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
2276 ± 46 µM YPD mediaaerobicBaker's yeastPMID: 7654310
1839 ± 37 µM YPG mediaaerobicBaker's yeastPMID: 7654310
788 ± 16 µM SD mediaaerobicBaker's yeastPMID: 7654310
876 ± 18 µM SG mediaaerobicBaker's yeastPMID: 7654310
525 ± 10 µM M (molasses)aerobicBaker's yeastPMID: 7654310
2802 ± 56 µM MA (molasses)aerobicBaker's yeastPMID: 7654310
1226 ± 24 µM MB (molasses)aerobicBaker's yeastPMID: 7654310
2014 ± 40 µM MAB (molasses)aerobicBaker's yeastPMID: 7654310
2770 ± 139 µM YEB media with 0.5 mM glucoseaerobicBaker's yeastExperimentally Determined
Not Available
3610 ± 664 µM Synthetic medium with 20 g/L glucoseaerobicBaker's yeastPMID: 12584756
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Martinez-Force, E., Benitez, T. (1995). "Effects of varying media, temperature, and growth rates on the intracellular concentrations of yeast amino acids." Biotechnol Prog 11:386-392.7654310
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Ryan, E. D., Kohlhaw, G. B. (1974). "Subcellular localization of isoleucine-valine biosynthetic enzymes in yeast." J Bacteriol 120:631-637.4616942
  • Hans, M. A., Heinzle, E., Wittmann, C. (2003). "Free intracellular amino acid pools during autonomous oscillations in Saccharomyces cerevisiae." Biotechnol Bioeng 82:143-151.12584756
  • Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71.18687109
  • Dickinson, J. R., Harrison, S. J., Hewlins, M. J. (1998). "An investigation of the metabolism of valine to isobutyl alcohol in Saccharomyces cerevisiae." J Biol Chem 273:25751-25756.9748245
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Kinoshita, Shukuo; Udaka, Shigezo. L-Valine production by fermentation. (1962), 2 pp.
External Links:
ResourceLink
CHEBI ID16414
HMDB IDHMDB00883
Pubchem Compound ID1182
Kegg IDC00183
ChemSpider ID6050
FOODB IDFDB012740
WikipediaValine
BioCyc IDVAL

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. Involved in cell cycle regulation
Gene Name:
BAT2
Uniprot ID:
P47176
Molecular weight:
41624.39844
Reactions
L-leucine + 2-oxoglutarate → 4-methyl-2-oxopentanoate + L-glutamate.
2-oxoglutaric acid + L-isoleucine → (S)-3-methyl-2-oxopentanoic acid + L-glutamic acid.
2-oxoglutaric acid + L-valine → 3-methyl-2-oxobutanoic acid + L-glutamic acid.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. Appears to be involved in the regulation of the transition from G1 to S phase in the cell cycle. High copy suppressor of a temperature-sensitive mutation in the ABC transporter, ATM1
Gene Name:
BAT1
Uniprot ID:
P38891
Molecular weight:
43595.69922
Reactions
L-leucine + 2-oxoglutarate → 4-methyl-2-oxopentanoate + L-glutamate.
2-oxoglutaric acid + L-isoleucine → (S)-3-methyl-2-oxopentanoic acid + L-glutamic acid.
2-oxoglutaric acid + L-valine → 3-methyl-2-oxobutanoic acid + L-glutamic acid.
General function:
Involved in nucleotide binding
Specific function:
ATP + L-valine + tRNA(Val) = AMP + diphosphate + L-valyl-tRNA(Val)
Gene Name:
VAS1
Uniprot ID:
P07806
Molecular weight:
125769.0
Reactions
ATP + L-valine + tRNA(Val) → AMP + diphosphate + L-valyl-tRNA(Val).

Transporters

General function:
Involved in transport
Specific function:
Permease for various amino acids as well as for GABA. Can also transport L-cysteine and beta-alanine
Gene Name:
GAP1
Uniprot ID:
P19145
Molecular weight:
65654.89844
General function:
Involved in transport
Specific function:
Permease for leucine, valine and isoleucine. Also transports cysteine, methionine, phenyalanine, tyrosine and tryptophan
Gene Name:
BAP2
Uniprot ID:
P38084
Molecular weight:
67669.60156
General function:
Involved in transport
Specific function:
High-affinity transport of valine and tyrosine. Low- affinity transport of tryptophan. Can also transport L-cysteine
Gene Name:
TAT1
Uniprot ID:
P38085
Molecular weight:
68756.89844
General function:
Involved in transport
Specific function:
Involved in transport of isoleucine, leucine, valine, cysteine, methionine, phenylalanine, tyrosine and tryptophan
Gene Name:
BAP3
Uniprot ID:
P41815
Molecular weight:
67364.39844
General function:
Involved in transport
Specific function:
Broad substrate range permease which transports asparagine and glutamine with intermediate specificity. Also transports Ala, Cys, Gly, Ile, Leu, Met, Phe, Ser, Thr, Tyr and Val. Important for the utilization of amino acids as a nitrogen source
Gene Name:
AGP1
Uniprot ID:
P25376
Molecular weight:
69670.70313