Escherichia coli K-12 substr. MG1655 Compound: phenylglyoxal

Synonyms: benzoylcarboxaldehyde, benzoylformaldehyde, phenylethanedione, α-oxobenzeneacetaldehyde, benzeneacetaldehyde, α-oxo-, monohydrate, glyoxal, phenyl-

Chemical Formula: C8H6O2

Molecular Weight: 134.13 Daltons

Monoisotopic Molecular Weight: 134.0367794368 Daltons

phenylglyoxal compound structure


InChI: InChI=1S/C8H6O2/c9-6-8(10)7-4-2-1-3-5-7/h1-6H


Unification Links: ChEBI:495613, ChemSpider:13470, PubChem:14090

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -26.29

Enzymes inhibited by phenylglyoxal, sorted by the type of inhibition, are:

Inhibitor (Irreversible) of: pyruvate oxidase [Koland82] Inhibitor (Mechanism unknown) of: acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase [Green84], 2-amino-3-ketobutyrate CoA ligase [Mukherjee92], threonine dehydrogenase [Epperly89], isocitrate dehydrogenase [Comment 1]

This compound has been characterized as an alternative substrate of the following enzymes: methylglyoxal reductase, glyoxalase, methylglyoxal reductase, methylglyoxal reductase (NADPH-dependent), methylglyoxal reductase, glyoxalase I


Epperly89: Epperly BR, Dekker EE (1989). "Inactivation of Escherichia coli L-threonine dehydrogenase by 2,3-butanedione. Evidence for a catalytically essential arginine residue." J Biol Chem 1989;264(31);18296-301. PMID: 2681195

Green84: Green PR, Bell RM (1984). "The triose-phosphate site of homogeneous reconstituted sn-glycerol-3-phosphate acyltransferase of Escherichia coli." Biochim Biophys Acta 1984;795(2);348-55. PMID: 6383480

Koland82: Koland JG, O'Brien TA, Gennis RB (1982). "Role of arginine in the binding of thiamin pyrophosphate to Escherichia coli pyruvate oxidase." Biochemistry 21(11);2656-600. PMID: 7046791

McKee89: McKee JS, Nimmo HG (1989). "Evidence for an arginine residue at the coenzyme-binding site of Escherichia coli isocitrate dehydrogenase." Biochem J 1989;261(1);301-4. PMID: 2673216

Mukherjee92: Mukherjee JJ, Dekker EE (1992). "Inactivation of Escherichia coli 2-amino-3-ketobutyrate CoA ligase by phenylglyoxal and identification of an active-site arginine peptide." Arch Biochem Biophys 299(1);147-53. PMID: 1444446

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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