| Entry |
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| Name |
2-hydroxymuconate tautomerase;
4-oxalocrotonate tautomerase (misleading);
4-oxalocrotonate isomerase (misleading);
cnbG (gene name);
praC (gene name);
xylH (gene name)
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| Class |
Isomerases;
Intramolecular oxidoreductases;
Interconverting keto- and enol-groups
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| Sysname |
(2Z,4E)-2-hydroxyhexa-2,4-dienedioate keto---enol isomerase
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| Reaction(IUBMB) |
(2Z,4E)-2-hydroxyhexa-2,4-dienedioate = (3E)-2-oxohex-3-enedioate
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| Reaction(KEGG) |
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| Substrate |
(2Z,4E)-2-hydroxyhexa-2,4-dienedioate
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| Product |
(3E)-2-oxohex-3-enedioate
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| Comment |
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 [6]. 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-enzymically [5].
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| History |
EC 5.3.2.6 created 2012
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| Pathway |
| ec01120 | Microbial metabolism in diverse environments |
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| Orthology |
| K01821 | 4-oxalocrotonate tautomerase |
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| Genes |
» show all
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| Reference |
1 |
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| Authors |
Whitman, C.P., Aird, B.A., Gillespie, W.R. and Stolowich, N.J. |
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| Title |
Chemical and enzymatic ketonization of 2-hydroxymuconate, a conjugated enol. |
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| Journal |
J Am Chem Soc 113:3154-3162 (1991) |
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| Reference |
2 |
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| Authors |
Whitman, C.P., Hajipour, G., Watson, R.J., Johnson, W.H., Jr., Bembenek, M.E. and Stolowich, N.J. |
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| Title |
Stereospecific ketonization of 2-hydroxymuconate by 4-oxalocrotonate tautomerase and 5-(carboxymethyl)-2-hydroxymuconate isomerase. |
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| Journal |
J Am Chem Soc 114:10104-10110 (1992) |
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| Reference |
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| Authors |
Subramanya HS, Roper DI, Dauter Z, Dodson EJ, Davies GJ, Wilson KS, Wigley DB |
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| Title |
Enzymatic ketonization of 2-hydroxymuconate: specificity and mechanism investigated by the crystal structures of two isomerases. |
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| Journal |
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| Reference |
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| Authors |
Stivers JT, Abeygunawardana C, Mildvan AS, Hajipour G, Whitman CP, Chen LH |
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| Title |
Catalytic role of the amino-terminal proline in 4-oxalocrotonate tautomerase: affinity labeling and heteronuclear NMR studies. |
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| Journal |
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| Sequence |
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| Reference |
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| Authors |
Wang SC, Johnson WH Jr, Czerwinski RM, Stamps SL, Whitman CP |
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| Title |
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. |
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| Journal |
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| Sequence |
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| Reference |
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| Authors |
Kasai D, Fujinami T, Abe T, Mase K, Katayama Y, Fukuda M, Masai E |
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| Title |
Uncovering the protocatechuate 2,3-cleavage pathway genes. |
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| Journal |
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| Sequence |
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| Other DBs |
| ExplorEnz - The Enzyme Database: | 5.3.2.6 |
| ExPASy - ENZYME nomenclature database: | 5.3.2.6 |
| BRENDA, the Enzyme Database: | 5.3.2.6 |
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| LinkDB |
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