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Escherichia coli K-12 substr. MG1655 Compound: 3-methyl-2-oxobutanoate

Synonyms: 2-oxo-3-methylbutanoate, 2-oxoisovalerate, α-keto-isovaleric acid, α-ketoisopentanoic acid, α-keto-isovalerate, α-oxoisovalerate, α-ketovaline, 2-keto-isovalerate, 2-ketovaline, α-keto-valine, 2-oxoisopentanoate, 2-keto-3-methylbutyric acid

Chemical Formula: C5H7O3

Molecular Weight: 115.11 Daltons

Monoisotopic Molecular Weight: 116.0473441231 Daltons

SMILES: CC(C(C([O-])=O)=O)C

InChI: InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)/p-1

InChIKey: InChIKey=QHKABHOOEWYVLI-UHFFFAOYSA-M

Unification Links: CAS:759-05-7 , ChEBI:11851 , ChemSpider:4375810 , HMDB:HMDB00019 , IAF1260:34011 , KEGG:C00141 , MetaboLights:MTBLC11851 , PubChem:5204641

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -111.26

Reactions known to consume the compound:

leucine biosynthesis :
3-methyl-2-oxobutanoate + acetyl-CoA + H2O → (2S)-2-isopropylmalate + coenzyme A + H+

Reactions known to produce the compound:

valine biosynthesis :
(R)-2,3-dihydroxy-3-methylbutanoate → 3-methyl-2-oxobutanoate + H2O

Reactions known to both consume and produce the compound:

alanine biosynthesis I :
pyruvate + L-valine ↔ L-alanine + 3-methyl-2-oxobutanoate
L-valine + 2-oxoglutarate ↔ 3-methyl-2-oxobutanoate + L-glutamate

phosphopantothenate biosynthesis I :
a 5,10-methylene-tetrahydrofolate + 3-methyl-2-oxobutanoate + H2O ↔ 2-dehydropantoate + a tetrahydrofolate

valine biosynthesis :
L-valine + 2-oxoglutarate ↔ 3-methyl-2-oxobutanoate + L-glutamate

Enzymes inhibited by 3-methyl-2-oxobutanoate, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: phenylalanine aminotransferase [Vartak91] , leucine aminotransferase [Vartak91] , tyrosine aminotransferase [Vartak91]


References

Vartak91: Vartak NB, Liu L, Wang BM, Berg CM (1991). "A functional leuABCD operon is required for leucine synthesis by the tyrosine-repressible transaminase in Escherichia coli K-12." J Bacteriol 173(12);3864-71. PMID: 1646790


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 18.5 on Tue Nov 25, 2014, biocyc14.