5.3.2.6: 2-hydroxymuconate tautomerase
This is an abbreviated version!
For detailed information about 2-hydroxymuconate tautomerase, go to the full flat file.
Word Map on EC 5.3.2.6
-
5.3.2.6
-
tautomerization
-
michael-type
-
trans-3-chloroacrylic
-
5-carboxymethyl-2-hydroxymuconate
-
2-oxo-3-pentynoate
-
stivers
-
dienolic
-
heterohexamer
-
2-hydroxy-2,4-pentadienoate
-
3-bromopyruvate
-
beta-alpha-beta
-
whitman
-
proline-based
-
3-chloroacrylic
-
cis-caad
-
meta-fission
-
cis-3-chloroacrylic
- 5.3.2.6
-
tautomerization
-
michael-type
-
trans-3-chloroacrylic
- 5-carboxymethyl-2-hydroxymuconate
- 2-oxo-3-pentynoate
-
stivers
-
dienolic
-
heterohexamer
- 2-hydroxy-2,4-pentadienoate
- 3-bromopyruvate
-
beta-alpha-beta
-
whitman
-
proline-based
-
3-chloroacrylic
- cis-caad
-
meta-fission
-
cis-3-chloroacrylic
Reaction
Synonyms
4-OT, 4-oxalocrotonate tautomerase, 4-oxalocrotonate tautomerase I, 4-oxalocrotonate tautomerase II, 4OT, AfDmpI, D-4-oxalocrotonate tautomerase, HpDmpI, L-4-oxalocrotonate tautomerase, OCA, PRAC, SAR1376, TomN, xylH, YwhB
ECTree
5.3.2.6 2-hydroxymuconate tautomeraseAdvanced search results
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results (Substrates Products
Substrates Products on EC 5.3.2.6 - 2-hydroxymuconate tautomerase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(1Z)-1-(nitromethylidene)-3a,4,5,6,7,7a-hexahydro-1H-indene + acetaldehyde
[1-(nitromethyl)-1H-inden-1-yl]acetaldehyde
-
-
-
-
?
(1Z)-4-methyl-1-nitropent-1-ene + acetaldehyde
5-methyl-3-(nitromethyl)hexanal
-
-
-
-
?
(2Z,4E)-2-hydroxyhexa-2,4-dienedioate
(2E)-5-oxohex-2-enedioic acid
-
-
-
-
?
(E)-1-nitro-2-(2-thienyl)ethene + isobutanal
2,2-dimethyl-4-nitro-3-(thiophen-2-yl)butanal
-
-
-
-
?
(E)-2-(furan-2-yl)nitroethene + isobutanal
3-(furan-2-yl)-2,2-dimethyl-4-nitrobutanal
-
-
-
-
?
(E)-2-(thiophen-2-yl)nitroethene + isobutanal
2,2-dimethyl-4-nitro-3-(thiophen-2-yl)butanal
-
-
-
-
?
1-chloro-4-[(Z)-2-nitroethenyl]benzene + acetaldehyde
3-(4-chlorophenyl)-4-nitrobutanal
-
-
-
-
?
1-fluoro-4-[(Z)-2-nitroethenyl]benzene + acetaldehyde
3-(4-fluorophenyl)-4-nitrobutanal
-
-
-
-
?
2-(cyclopentyloxy)-1-methoxy-4-[(Z)-2-nitroethenyl]benzene + acetaldehyde
3-[3-(cyclopentyloxy)-4-methoxyphenyl]-4-nitrobutanal
-
-
-
-
?
2-chloro-beta-nitrostyrene + acetaldehyde
3-(2-chlorophenyl)-4-nitrobutanal
-
-
51% yield
-
?
2-methoxy-5-[(Z)-2-nitroethenyl]phenol + acetaldehyde
3-(3-hydroxy-4-methoxyphenyl)-4-nitrobutanal
-
-
-
-
?
3,4-(methylenedioxy)-beta-nitrostyrene + isobutanal
(3E)-3-(2H-1,3-benzodioxol-5-yl)-2,2-dimethyl-4-nitrobut-3-enal
-
-
-
-
?
4-chloro-beta-nitrostyrene + acetaldehyde
3-(4-chlorophenyl)-4-nitrobutanal
-
-
38% yield
-
?
4-fluoro-beta-nitrostyrene + acetaldehyde
3-(4-fluorophenyl)-4-nitrobutanal
-
-
31% yield
-
?
4-vinyl-2,3-dihydropyrrole-2-carboxylic acid
4-ethylidene-3,4-dihydropyrrole-2-carboxylic acid
-
-
-
-
r
5-(methyl)-2-hydroxymuconate
5-(methyl)-2-oxo-3-hexenedioate
-
-
-
?
acetaldehyde + (1Z)-4-methyl-1-nitropent-1-ene
6-methyl-4-(nitromethyl)heptan-2-one
-
-
-
r
acetaldehyde + 1-chloro-4-[(E)-2-nitroethenyl]benzene
4-(4-chlorophenyl)-5-nitropentan-2-one
-
-
-
r
acetaldehyde + 1-fluoro-4-[(E)-2-nitroethenyl]benzene
4-(4-fluorophenyl)-5-nitropentan-2-one
-
-
-
r
acetaldehyde + 2-(cyclopentyloxy)-1-methoxy-4-[(E)-2-nitroethenyl]benzene
4-[3-(cyclopentyloxy)-4-methoxyphenyl]-5-nitropentan-2-one
-
-
-
r
acetaldehyde + 2-methoxy-5-[(E)-2-nitroethenyl]phenol
4-(3-hydroxy-4-methoxyphenyl)-5-nitropentan-2-one
-
-
-
r
acetaldehyde + 4-[(E)-2-nitroethenyl]phenol
4-(4-hydroxyphenyl)-5-nitropentan-2-one
-
-
-
r
acetaldehyde + [(E)-2-nitroethenyl]benzene
5-nitro-4-phenylpentan-2-one
-
-
-
r
acetaldehyde + [(Z)-2-nitroethenyl]benzene
(3S)-4-nitro-3-phenylbutanal
-
-
-
-
?
beta-nitrostyrene + acetaldehyde
4-nitro-3-phenyl-butanal
-
-
60% yield
-
?
beta-nitrostyrene + isobutanal
2,2-dimethyl-4-nitro-3-phenylbutanal
-
-
-
-
?
butanal + [(E)-2-nitroethenyl]benzene
3-ethyl-5-nitro-4-phenylpentan-2-one
-
-
-
r
butanal + [(Z)-2-nitroethenyl]benzene
(2R,3S)-2-ethyl-4-nitro-3-phenylbutanal
-
-
-
-
?
heptanal + [(Z)-2-nitroethenyl]benzene
(2R)-2-[(1S)-2-nitro-1-phenylethyl]heptanal
-
-
-
-
?
hexanal + [(Z)-2-nitroethenyl]benzene
(2R)-2-[(1S)-2-nitro-1-phenylethyl]hexanal
-
-
-
-
?
isobutanal + beta-nitrostyrene
2,2-dimethyl-4-nitro-3-phenylbutanal + 4-nitro-3-phenylbutanal
-
-
-
-
?
octanal + [(Z)-2-nitroethenyl]benzene
(2R)-2-[(1S)-2-nitro-1-phenylethyl]octanal
-
-
-
-
?
pentanal + [(Z)-2-nitroethenyl]benzene
(2R)-2-[(1S)-2-nitro-1-phenylethyl]pentanal
-
-
-
-
?
propanal + [(Z)-2-nitroethenyl]benzene
(2R,3S)-2-methyl-4-nitro-3-phenylbutanal
-
-
-
-
?
trans-p-chloro-beta-nitrostyrene + isobutanal
3-(4-chlorophenyl)-2,2-dimethyl-4-nitrobutanal
-
-
-
-
?
[(Z)-2-nitroethenyl]benzene + acetaldehyde
4-nitro-3-phenylbutanal
-
-
-
-
?
(2Z,4E)-2-hydroxyhexa-2,4-dienedioate
(2E)-5-oxohex-2-enedioate
-
-
-
?
(2Z,4E)-2-hydroxyhexa-2,4-dienedioate
(2E)-5-oxohex-2-enedioate
-
1,3- and 1,5-keto-enol tautomerization reactions are observed for 2-hydroxy-2,4-hexadienedioate. YwhB converts it to the 3S isomer of 2-oxo-4-hexenedioate in a highly stereoselective manner
main product
-
?
(2Z,4E)-2-hydroxyhexa-2,4-dienedioate
(3E)-2-oxohex-3-enedioate
-
-
-
?
(2Z,4E)-2-hydroxyhexa-2,4-dienedioate
(3E)-2-oxohex-3-enedioate
-
-
-
-
?
(2Z,4E)-2-hydroxyhexa-2,4-dienedioate
(3E)-2-oxohex-3-enedioate
-
-
-
-
r
(2Z,4E)-2-hydroxyhexa-2,4-dienedioate
(3E)-2-oxohex-3-enedioate
-
-
-
-
r
(2Z,4E)-2-hydroxyhexa-2,4-dienedioate
(3E)-2-oxohex-3-enedioate
-
-
-
?
(2Z,4E)-2-hydroxyhexa-2,4-dienedioate
(3E)-2-oxohex-3-enedioate
-
-
-
-
r
(2Z,4E)-2-hydroxyhexa-2,4-dienedioate
(3E)-2-oxohex-3-enedioate
-
-
-
r
(2Z,4E)-2-hydroxyhexa-2,4-dienedioate
(3E)-2-oxohex-3-enedioate
-
-
-
r
(2Z,4E)-2-hydroxyhexa-2,4-dienedioate
(3E)-2-oxohex-3-enedioate
-
-
-
r
2-hydroxy-2,4-hexadienedioate
2-oxo-3,4-hexenedioate
-
4-OT with 2-hydroxy-2,4-hexadienedioate in D2O results in a racemic mixture of 2-oxo-[3-2H]-4-hexenedioate, suggesting that 4-OT may not catalyze a 1,3-keto-enol tautomerization reaction using this dienol
-
-
?
2-hydroxy-2,4-hexadienedioate
2-oxo-3,4-hexenedioate
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
-
4-OT with 2-hydroxy-2,4-hexadienedioate in D2O results in a racemic mixture of 2-oxo-[3-2H]-4-hexenedioate, suggesting that 4-OT may not catalyze a 1,3-keto-enol tautomerization reaction using this dienol
-
-
?
2-hydroxy-2,4-hexadienedioate
2-oxo-3-hexenedioate
i.e. 2-hydroxymuconate
-
-
r
2-hydroxy-2,4-hexadienedioate
2-oxo-3-hexenedioate
i.e. 2-hydroxymuconate, the enzyme catalyzes the conversion of 2-hydroxy-2,4-hexadienedioate (or 2-hydroxymuconate) to 2-oxo-3-hexenedioate, where Pro-1 functions as a general base and shuttles a proton from the 2-hydroxyl group of the substrate to the C-5 position of the product. hh4-OT requires the amino-terminal proline and two arginines for the conversion of 2-hydroxymuconate to the product
-
-
r
2-hydroxy-2,4-hexadienedioate
2-oxo-3-hexenedioate
i.e. 2-hydroxymuconate
-
-
r
2-hydroxy-2,4-hexadienedioate
2-oxo-3-hexenedioate
i.e. 2-hydroxymuconate, the enzyme catalyzes the conversion of 2-hydroxy-2,4-hexadienedioate (or 2-hydroxymuconate) to 2-oxo-3-hexenedioate, where Pro-1 functions as a general base and shuttles a proton from the 2-hydroxyl group of the substrate to the C-5 position of the product. hh4-OT requires the amino-terminal proline and two arginines for the conversion of 2-hydroxymuconate to the product
-
-
r
2-hydroxy-2,4-hexadienedioate
2-oxo-3-hexenedioate
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
-
-
-
-
?
2-hydroxy-4-trans-hexenedioate
?
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
-
-
-
-
?
2-hydroxymuconate
2-oxo-3-(E)-hexenedioate
-
stereospecific ketonization, a reaction of EC 5.3.2.6, is also catalyzed by 5-(carboxymethyl)-2-hydroxymuconate isomerase, EC 5.3.3.10
-
-
?
2-hydroxymuconate
2-oxo-3-(E)-hexenedioate
-
stereospecific ketonization, a reaction of EC 5.3.2.6, is also catalyzed by 5-(carboxymethyl)-2-hydroxymuconate isomerase, EC 5.3.3.10
-
-
?
2-hydroxymuconate
2-oxo-3-(E)-hexenedioate
-
stereospecific ketonization
-
-
?
2-hydroxymuconate
2-oxo-3-(E)-hexenedioate
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
-
stereospecific ketonization
-
-
?
2-hydroxymuconate
2-oxo-3-hexenedioate
-
the conjugated enol, 2-hydroxymuconate is an unusually stable dienol that is reportedly generated in the course of bacterial catabolism of catechol by the enzymes of the meta-fission pathway
the dienol ketonizes chemically in aqueous solution and enzymatically by the action of 4-oxalocrotonate tautomerase to either the beta,gamma-unsaturated ketone or its alpha,beta-conjugated isomer 2-oxo-3-trans-hexenedioate
-
r
2-hydroxymuconate
2-oxo-3-hexenedioate
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
-
ketonization
-
-
?
2-hydroxymuconate
2-oxo-3-hexenedioate
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
-
ketonization
-
-
r
2-hydroxymuconate
2-oxo-3-hexenedioate
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
-
the conjugated enol, 2-hydroxymuconate is an unusually stable dienol that is reportedly generated in the course of bacterial catabolism of catechol by the enzymes of the meta-fission pathway
the dienol ketonizes chemically in aqueous solution and enzymatically by the action of 4-oxalocrotonate tautomerase to either the beta,gamma-unsaturated ketone or its alpha,beta-conjugated isomer 2-oxo-3-trans-hexenedioate
-
r
2-oxo-3-hexenedioate
2-oxo-3-trans-hexenedioate
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
-
-
-
-
?
2-oxo-4(E)-hexenedioate
2-oxo-3(E)-hexenedioate
-
1,3-allylic isomerization
-
-
?
2-oxo-4(E)-hexenedioate
2-oxo-3(E)-hexenedioate
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
-
1,3-allylic isomerization
-
-
?
2-oxo-4-hexenedioate
2-oxo-3-hexenedioate
-
isomerization of unconjugated 2-oxo acids such as 2-oxo-4-hexenedioate, to its conjugated isomer via dienol intermediate 2-hydroxy-2,4-hexadienedioate, i.e. 2-hydroxymuconate
-
-
?
2-oxo-4-hexenedioate
2-oxo-3-hexenedioate
-
ketonization process via dienol intermediate 2-hydroxymuconate and with Pro1 as a general base, one-proton transfer mechanism
-
-
?
2-oxo-4-hexenedioate
2-oxo-3-hexenedioate
-
via dienol intermediate 2-hydroxymuconate
-
-
?
2-oxo-4-hexenedioate
2-oxo-3-hexenedioate
-
via the intermediate 2-hydroxy-2,4-hexadienedioate, i.e. 2-hydroxymuconate
-
-
?
2-oxo-4-hexenedioate
2-oxo-3-hexenedioate
-
the enzyme converts the unconjugated enone to the conjugated enone via a dienolic intermediate 2-hydroxymuconate, Pro1 serves as the general base, and both Arg11 and Arg39 function in substrate binding and catalysis in an otherwise hydrophobic active site. Anticooperativity during catalysis
-
-
r
2-oxo-4-hexenedioate
2-oxo-3-hexenedioate
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
-
isomerization of unconjugated 2-oxo acids such as 2-oxo-4-hexenedioate, to its conjugated isomer via dienol intermediate 2-hydroxy-2,4-hexadienedioate, i.e. 2-hydroxymuconate
-
-
?
2-oxo-4-hexenedioate
2-oxo-3-hexenedioate
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
-
via dienol intermediate 2-hydroxymuconate
-
-
?
2-oxo-4-hexenedioate
2-oxo-3-hexenedioate
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
-
via the intermediate 2-hydroxy-2,4-hexadienedioate, i.e. 2-hydroxymuconate
-
-
?
additional information
?
-
-
YwhB has a relatively non-specific 1,3- and 1,5-keto-enol tautomerase activity, converting 2-hydroxy-2,4-pentadienoate to 2-oxo-4-pentenoate, and phenylenolpyruvate to phenylpyruvate. But YwhB is a more efficient 1,3-keto-enol tautomerase than it is a 1,5-keto-enol tautomerase, and residues Pro-1 and Arg-11 are critical residues for these two activities
-
-
?
additional information
?
-
hh4-OT does not exhibit the low-level activity of another tautomerase superfamily member, the heterohexamer trans-3-chloroacrylic acid dehalogenase, no activity with trans-3-chloroacrylic acid
-
-
?
additional information
?
-
hh4-OT does not exhibit the low-level activity of another tautomerase superfamily member, the heterohexamer trans-3-chloroacrylic acid dehalogenase, no activity with trans-3-chloroacrylic acid
-
-
?
additional information
?
-
-
hh4-OT does not exhibit the low-level activity of another tautomerase superfamily member, the heterohexamer trans-3-chloroacrylic acid dehalogenase, no activity with trans-3-chloroacrylic acid
-
-
?
additional information
?
-
-
ketonization of two monoacid substrates, 2-hydroxy-2,4-pentadienoate and phenylenolpyruvate, produces a mixture of stereoisomers, 2-keto-3-[2H]-4-pentenoate and 3-[2H]-phenylpyruvate, where the (3R)-isomers predominate
-
-
?
additional information
?
-
-
the achiral substrate 2-hydroxymuconate is processed with equal efficiency by either the D- or the L-enzyme, stereochemical analysis of the D-4OT-catalyzed reaction, overviewn
-
-
?
additional information
?
-
-
no activity with (E)-2-cyclohexyl-1-nitroethene
-
-
?
additional information
?
-
-
the enzyme also has a low level trans-3-chloroacrylic acid dehalogenase activity
-
-
?
additional information
?
-
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
-
ketonization of two monoacid substrates, 2-hydroxy-2,4-pentadienoate and phenylenolpyruvate, produces a mixture of stereoisomers, 2-keto-3-[2H]-4-pentenoate and 3-[2H]-phenylpyruvate, where the (3R)-isomers predominate
-
-
?
additional information
?
-
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
-
substrate specificity, overview
-
-
?
additional information
?
-
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
-
the achiral substrate 2-hydroxymuconate is processed with equal efficiency by either the D- or the L-enzyme, stereochemical analysis of the D-4OT-catalyzed reaction, overviewn
-
-
?
additional information
?
-
-
4-oxalocrotonate tautomerase catalyzes the isomerization of unsaturated 2-oxo acids, converting unconjugated ketones to the conjugated isomers via a dienolic intermediate
-
-
?
additional information
?
-
-
4-oxalocrotonate tautomerase catalyzes the isomerization of unsaturated 2-oxo acids, converting unconjugated ketones to the conjugated isomers via a dienolic intermediate
-
-
?
additional information
?
-
substrate specificity, overview
-
-
?
