EC 184.108.40.206 - 2-hydroxymuconate tautomerase
IntEnz Enzyme Nomenclature
4-oxalocrotonate isomerase [misleading]
cnbG (gene name)
praC (gene name)
xylH (gene name)
33431 [IUBMB](2Z,4E)-2-hydroxyhexa-2,4-dienedioate(2Z,4E)-2-hydroxyhexa-2,4-dienedioateName origin: UniProt - CHECKED (C)Formula: C6H4O5
Charge: -2ChEBI compound status: CHECKED (C)<?>
Involved in the meta-cleavage pathway for the degradation of phenols, modified phenols and catechols. The enol form (2Z,4E)-2-hydroxyhexa-2,4-dienedioate is produced as part of this pathway and is converted to the keto form (3E)-2-oxohex-3-enedioate by the enzyme . Another keto form, (4E)-2-oxohex-4-enedioate (4-oxalocrotonate), was originally thought to be produced by the enzyme [1,2] but later shown to be produced non-enzymatically .
Links to other databases
Chemical and enzymatic ketonization of 2-hydroxymuconate, a conjugated enol.J. Am. Chem. Soc. 113: 3154-3162 (1991).
Stereospecific ketonization of 2-hydroxymuconate by 4-oxalocrotonate tautomerase and 5-(carboxymethyl)-2-hydroxymuconate isomerase.J. Am. Chem. Soc. 114: 10104-10110 (1992).
Enzymatic ketonization of 2-hydroxymuconate: specificity and mechanism investigated by the crystal structures of two isomerases.Biochemistry 35: 792-802 (1996). [PMID: 8547259]
Catalytic role of the amino-terminal proline in 4-oxalocrotonate tautomerase: affinity labeling and heteronuclear NMR studies.Biochemistry 35: 803-813 (1996). [PMID: 8547260]
Kinetic and stereochemical analysis of YwhB, a 4-oxalocrotonate tautomerase homologue in Bacillus subtilis: mechanistic implications for the YwhB- and 4-oxalocrotonate tautomerase-catalyzed reactions.Biochemistry 46: 11919-11929 (2007). [PMID: 17902707]
Uncovering the protocatechuate 2,3-cleavage pathway genes.J. Bacteriol. 191: 6758-6768 (2009). [PMID: 19717587]
[EC 220.127.116.11 created 2012]