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Information on EC 1.3.1.31 - 2-enoate reductase
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EC Tree
1.3.1.31 2-enoate reductaseIUBMB Comments
An iron-sulfur-flavoprotein (FAD). Acts (in the reverse direction) on a wide range of alkyl and aryl alphabeta-unsaturated carboxylate ions; but-2-enoate was the best substrate tested.
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Word Map
- 1.3.1.31
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alpha,beta-unsaturated
- tyrobutyricum
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spec
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bioreduction
- kluyveri
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beta-unsaturated
- methylviologen
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
enoate reductase, yellow enzyme, lacer, 2-enoate reductase, nadph dehydrogenase 1, achr-oye4, er-ca, achr-oye3, kpner, er-bc, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Achr-OYE4
acylate:NAD+ DELTA2 oxidoreductase
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-
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enoate reductase
ERED
fldZ
NAD(P)H-dependent enoate reductase
NADH-dependent 2-enoate reductase
old yellow enzyme
OYE
reductase, 2-enoate
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XenA
xenobiotic reductase A showing enoate reductase activity toward 2-cyclohexen-1-one
YqjM
enoate reductase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
butanoate + NAD+ = but-2-enoate + NADH + H+
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butanoate + NAD+ = but-2-enoate + NADH + H+
ping-pong mechanism in aqueous solution
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butanoate + NAD+ = but-2-enoate + NADH + H+
enzyme kinetics in reversed micelles
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dehydrogenation
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oxidation
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redox reaction
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reduction
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
butanoate:NAD+ DELTA2-oxidoreductase
An iron-sulfur-flavoprotein (FAD). Acts (in the reverse direction) on a wide range of alkyl and aryl alphabeta-unsaturated carboxylate ions; but-2-enoate was the best substrate tested.
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CAS REGISTRY NUMBER
COMMENTARY
70712-51-5
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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
(+)-carvone + NADPH
?
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 100%, ee: 97%
-
-
?
(-)-carvone + NADPH
?
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 100%, ee: 95%
-
-
?
(1-nitroprop-1-en-2-yl)benzene + NADP+
[(2R)-1-nitropropan-2-yl]benzene + NADPH + H+
-
-
product of isoform OPR1
-
?
(2E)-2-benzylidenecyclohexanone + NADPH
?
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 92%, ee: 51%
-
-
?
(2E)-2-benzylidenecyclopentanone + NADPH
?
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 4%, ee: racemate
-
-
?
(2E)-2-cyano-3-phenylprop-2-enoic acid + NADPH
2-cyano-3-phenylpropanoic acid + NADP+
conversion rate measured using HPLC after 48 h. Conversion: 83%, ee: racemic
-
-
?
(2E)-2-methyl-3-phenylacrylic acid + electron donor
2-methyl-3-phenylpropanoic acid + electron acceptor
-
-
-
-
?
(2E)-2-methyl-3-phenylbut-2-enoic acid + electron donor
2-methyl-3-phenylbutanoic acid + electron acceptor
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-
-
-
?
(2E)-2-methylbut-2-enedioic acid + electron donor
2-methylbutanedioic aicd + electron acceptor
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-
-
-
?
(2E)-2-methylpent-2-enal + NADH + H+
(2R)-2-methylpentanal + NAD+
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-
-
-
?
(2E)-3,7-dimethylocta-2,6-dienal + NADH + H+
3,7-dimethyloct-6-enal + NAD+
-
-
-
-
?
(2E)-3-phenylacrylic acid + electron donor
3-phenylpropanoic acid + electron acceptor
-
-
-
-
?
(2E)-4-methoxy-2-methyl-4-oxobut-2-enoic acid + electron donor
4-methoxy-2-methyl-4-oxobutanoic acid + electron acceptor
-
-
-
-
?
(2E)-4-methoxy-3-methyl-4-oxobut-2-enoic acid + electron donor
4-methoxy-3-methyl-4-oxobutanoic acid + electron acceptor
-
-
-
-
?
(2E,4E)-2,3,5,8-tetramethylnona-2,4,7-trienoic acid + electron donor
? + electron acceptor
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-
-
-
?
(2E,4E)-2,3-dimethylhexa-2,4-dienoic acid + electron donor
? + electron acceptor
-
-
-
-
?
(2E,6Z)-nona-2,6-dienal + NADH + H+
?
-
relative activity: 62.7%
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?
(2Z)-3-(4-chlorophenyl)-3-cyanoprop-2-enoic acid + NADPH
(R)-3-(4-chlorophenyl)-3-cyano-propanoic acid + NADP+
conversion rate measured using HPLC after 48 h. Conversion: 80%, ee: 94% (R)
-
-
?
(5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one + NADH + H+
(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one + NAD+
-
-
-
-
?
(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one + NADH + H+
(2R,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one + NAD+
-
-
-
-
?
(E)-(2-nitroprop-1-en-1-yl)benzene + NADP+
[(3S)-3-nitrobutyl]benzene + NADPH + H+
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-
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?
(E)-2,5-dimethoxycinnamate + NADH
3-(2,5-dimethoxyphenyl)propionate + NAD+
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?
(E)-2-decenal + NADH + H+
decanal + NAD+
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relative activity: 90%
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?
(E)-2-hexen-1-al + NADH + H+
hexanal + NAD+
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relative activity: 100%
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-
?
(E)-2-methyl-2-butenal + NADH + H+
2-methylbutanal + NAD+
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relative activity: 59.2%
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?
(E)-2-methyl-2-butenoate + 4,5-dihydroxyanthraquinone-2-carboxylic acid
2-methylbutanoate + ?
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?
(E)-2-methyl-3-phenyl-2-propenoate + reduced methyl viologen
(R)-2-methyl-3-phenylpropanoate + methyl viologen
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?
(E)-2-nonenal + NADH + H+
nonanal + NAD+
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relative activity: 57%
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?
(E)-2-octenal + NADH + H+
octanal + NAD+
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relative activity: 75.4%
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?
(E)-2-oxo-4-phenyl-3-butenoate + NADH
2-oxo-4-phenyl-3-butanoate + NAD+
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18% of the activity with butenoate
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-
?
(E)-2-pentenal + NADH + H+
2-pentanone + NAD+
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relative activity: 45%
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?
(E)-3-methyl-2-oxo-4-phenyl-3-butenoate + NADH
3-methyl-2-oxo-4-phenyl-3-butenoate + NAD+
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27% of the activity with butenoate
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?
(E)-3-nonen-2-one + NADH + H+
nonan-2-one + NAD+
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relative activity: 36.6%
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-
?
(E)-3-nonen-2-one + NADPH
nonan-2-one + NADP+
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relative activity: 61.6%
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?
(E)-4-(2,4-dimethoxyphenyl)but-3-en-2-one + NAD+
4-(2,4-dimethoxyphenyl)butan-2-one + NADH + H+
(E)-4-(4'-isopropylphenyl)but-3-en-2-one + NAD+
4-(4-isopropylphenyl)butan-2-one + NADH + H+
(E)-4-(benzo[1,3]dioxol-5-yl)but-3-en-2-one + NAD+
4-(1,3-benzodioxol-5-yl)butan-2-one + NADH + H+
(E)-ethyl 2-methyl-4-oxopent-2-enoate + NADP+
ethyl (2R)-2-methyl-4-oxopentanoate + NADPH + H+
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?
(Z)-2-bromocinnamate + NADH
3-(2-bromophenyl)propionate + NAD+
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?
(Z)-2-chloro-3-(p-chlorophenyl)acrylate + NADH
2-chloro-3-(4-chlorophenyl)propionate + NAD+
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?
(Z)-3-cyano-3-phenyl-propenoic acid + NADPH + H+
(R)-3-cyano-3-phenylpropanoic acid + NADP+
highest enantiomeric excess of 98% ee is achieved at a glucose concentration of 1% (w/v) with a 47% conversion for an 18 h reaction. Concentration of 2-propanol also affects the activity and selectivity of the reaction, and a concentration of 5% (v/v) results in the best substrate conversion and ee value of product. Conversion rate measured using HPLC after 48 h. Conversion: 80%, ee: 98% (R)
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?
1,3-dimethyl-1H-pyrrole-2,5-dione + NADPH
?
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biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 99%
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?
1-(cyclohex-1-en-1-yl)ethanone + NADPH
?
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biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 71%, ee: not applicable
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?
1-(cyclopent-1-en-1-yl)ethanone + NADPH
?
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biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 30%, ee: not applicable
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?
1-(prop-2-en-1-yl)-1H-pyrrole-2,5-dione + NADPH
?
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biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: not applicable
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?
1-benzyl-1H-pyrrole-2,5-dione + NADH + H+
1-benzylpyrrolidine-2,5-dione + NAD+
-
-
-
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?
1-benzyl-3-methyl-1H-pyrrole-2,5-dione + NADH + H+
(3R)-1-benzyl-3-methylpyrrolidine-2,5-dione + NAD+
-
-
-
-
?
1-butyl-3-methyl-1H-pyrrole-2,5-dione + NADPH
?
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 99%
-
-
?
1-ethyl-3-methyl-1H-pyrrole-2,5-dione + NADPH
?
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biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 99%
-
-
?
12-phenyldodec-2-enoic acid + electron donor
12-phenyldodecanoic acid + electron acceptor
-
-
-
-
?
2,3-dimethylmaleimide + NADH
trans-dimethylsuccinimide + NAD+
-
-
-
-
?
2,6,6-trimethyl-2-cyclohexen-1,4-dione + NADPH
?
-
relative activity: 103%
-
-
?
2,6,6-trimethylcyclohex-2-ene-1,4-dione + NADH + H+
(6R)-2,2,6-trimethylcyclohexane-1,4-dione + NAD+
-
-
-
-
?
2-cyclohexen-1-one + NADH + H+
cyclohexanone + NAD+
-
relative activity: 830%
-
-
?
2-hydroxycyclopent-2-en-1-one + NADH + H+
(2S)-2-hydroxycyclopentan-1-one + NAD+
-
-
-
-
?
2-isopropyl-5-methyl-2-hexenal + NADH + H+
2-isopropyl-5-methylhexanal + NAD+
-
relative activity: 15.5%
-
-
?
2-methyl-2-cyclopenten-1-one + NADH + H+
?
-
relative activity: 62.7%
-
-
?
2-methylcyclohexenone + NAD(P)H + H+
(R)-2-methylcyclohexanone + NAD(P)+
-
NAD(P)H donates two electrons and one proton directly to the enzyme-bound FMN moiety. A stepwise reduction by successive transfer of electron yields a single-electron reduced semiquinone state of FMN, which can be fully reduced by taking an additional electron. Direct transfer of photoexcited electrons from 4,5,6,7-tetrachloro-2',4',5',7'-tetraiodofluorescein (RB) to a flavin-containing OYE homologue from Thermus scotoductus upon visible light irradiation with triethanolamine (TEOA) as an electron donor is described. Successive transfer of electrons reduces the enzyme-bound FMN moiety and drives the enantioselective conversion of 2-methylcyclohexenone into enantiopure (R)-2-methycyclohexanone (ee more than 99%)
-
-
?
2-methylcyclopent-2-enone + NADPH
?
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 92%, ee: 52%
-
-
?
3-methyl-1-(prop-2-en-1-yl)-1H-pyrrole-2,5-dione + NADPH
?
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 99%
-
-
?
3-methyl-1-phenyl-1H-pyrrole-2,5-dione + NADPH
(R)-N-phenyl-2-methylsuccinimide + NADP+
conversion rate measured using HPLC after 48 h. Conversion: 99%, ee: 99% (R)
-
-
?
3-methyl-1-propyl-1H-pyrrole-2,5-dione + NADPH
?
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 99%
-
-
?
3-methyl-2-cyclopentenone + NADH + H+
?
-
relative activity: 31%
-
-
?
4-(1,3-benzodioxol-5-yl)butan-2-one + NAD+
(S)-4-(1,3-benzodioxol-5-yl)butan-2-ol + NADH + H+
-
-
-
-
?
4-(4-methoxyphenyl)-3-buten-2-one + NAD+
4-(4-methoxyphenyl)-butan-2-one + NADH + H+
-
-
-
-
?
4-coumaric acid + NAD+
3-(4-hydroxyphenyl)propionic acid + NADH + H+
-
-
-
-
?
5-benzylidenethiazolidine-2,4-dione + NADH
(5R)-5-benzyl-1,3-thiazolidine-2,4-dione + NAD+
beta-ionone + NADPH + H+
dihydro-beta-ionone + NADP+
DBR1 has high selectivity to hydrogenated the 10,11-unsaturated double bond of beta-ionone as well as high catalytic efficiency for the conversion of beta-ionone to dihydro-beta-ionone
-
-
?
butenoate + reduced methyl viologen
butanoate + methyl viologen
-
-
-
-
?
diethyl (2Z)-2-methylbut-2-enedioate + NADPH
?
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 99%
-
-
?
dimethyl (2E)-2-methylbut-2-enedioate + NAD(P)H
dimethyl (2R)-2-methylbutanedioate + dimethyl (2S)-2-methylbutanedioate + NAD(P)+
dimethyl (2Z)-2-methylbut-2-enedioate + NAD(P)H
dimethyl (2R)-2-methylbutanedioate + NAD(P)+
dimethyl (2Z)-2-methylbut-2-enedioate + NADPH
?
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 98%
-
-
?
dimethyl 2-methylidenebutanedioate + NADPH
?
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 19%, ee: 90%
-
-
?
ethyl (2Z)-3-nitro-2-phenylprop-2-enoate + NADPH
ethyl (2R)-3-nitro-2-phenylpropanoate + NADP+
conversion rate measured using HPLC after 48 h. Conversion: 40%, ee: 45% (R)
-
-
?
hexa-2,4-dienoic acid + electron donor
? + electron acceptor
-
-
-
-
?
methyl 2-phenylacrylate + NADP+
methyl (2R)-2-methyl-3-phenylpropanoate + NADPH + H+
-
-
-
-
?
oct-2-en-4-ynoic acid + electron donor
? + electron acceptor
-
-
-
-
?
phenylmaleic anhydride + NADH + H+
?
-
relative activity: 402%
-
-
?
[(1E)-1-nitroprop-1-en-2-yl]benzene + NADPH
(S)-1-nitro-2-phenylpropane + NADP+
conversion rate measured using HPLC after 48 h. Conversion: 87%, ee: 97% (S)
-
-
?
[(1E)-2-nitroprop-1-en-1-yl]benzene + NADPH
1-phenyl-2-nitropropane + NADP+
conversion rate measured using HPLC after 48 h. Conversion: 60%, ee: racemic
-
-
?
(+)-costunolide + NADPH
11(S),13-dihydrocostunolide + NADP+
-
part of the metabolization of (+)-costunolide to leucodin, overview
-
-
?
(1-nitroprop-1-en-2-yl)benzene + NADP+
[(2S)-1-nitropropan-2-yl]benzene + NADPH + H+
-
-
-
-
?
(1-nitroprop-1-en-2-yl)benzene + NADP+
[(2S)-1-nitropropan-2-yl]benzene + NADPH + H+
-
-
product of isoform OPR3
-
?
(4R)-(-)-carvone + ?
(1R,4R)-dihydrocarvone + ?
-
Bacillus sp. FM18civ1 has preference for (4R)-(-)-carvone over (4S)-(+)-carvone
-
-
?
(4R)-(-)-carvone + ?
(1R,4R)-dihydrocarvone + ?
Bacillus sp. (in: Bacteria) FM18civ1
-
Bacillus sp. FM18civ1 has preference for (4R)-(-)-carvone over (4S)-(+)-carvone
-
-
?
(4R)-(-)-carvone + ?
(1R,4R)-dihydrocarvone + ?
-
Pseudomonas proteolytica FM18Mci1 has preference for the 4S-(-)-carvone over (4R)-(+)-carvone, reaching a conversion 95% in 24 h
-
-
?
(4R)-(-)-carvone + ?
(1R,4R)-dihydrocarvone + ?
Pseudomonas proteolytica FM18Mci1
-
Pseudomonas proteolytica FM18Mci1 has preference for the 4S-(-)-carvone over (4R)-(+)-carvone, reaching a conversion 95% in 24 h
-
-
?
(4S)-(+)-carvone + ?
(1R,4S)-dihydrocarvone + ?
-
Bacillus sp. FM18civ1 has preference for (4R)-(-)-carvone over (4S)-(+)-carvone
-
-
?
(4S)-(+)-carvone + ?
(1R,4S)-dihydrocarvone + ?
Bacillus sp. (in: Bacteria) FM18civ1
-
Bacillus sp. FM18civ1 has preference for (4R)-(-)-carvone over (4S)-(+)-carvone
-
-
?
(4S)-(+)-carvone + ?
(1R,4S)-dihydrocarvone + ?
-
Pseudomonas proteolytica FM18Mci1 has preference for the 4S-(-)-carvone over (4R)-(+)-carvone, reaching a conversion 95% in 24 h
-
-
?
(4S)-(+)-carvone + ?
(1R,4S)-dihydrocarvone + ?
Pseudomonas proteolytica FM18Mci1
-
Pseudomonas proteolytica FM18Mci1 has preference for the 4S-(-)-carvone over (4R)-(+)-carvone, reaching a conversion 95% in 24 h
-
-
?
(E)-1-nitro-2-phenylpropene + NADH + H+
(R)-1-nitro-2-phenylpropane + NAD+
(E)-1-nitro-2-phenylpropene is reduced to enantiopure (R)-1-nitro-2-phenylpropane with a yield of 90%
-
-
?
(E)-1-nitro-2-phenylpropene + NADH + H+
(R)-1-nitro-2-phenylpropane + NAD+
Clostridium sporogenes DSM 795
(E)-1-nitro-2-phenylpropene is reduced to enantiopure (R)-1-nitro-2-phenylpropane with a yield of 90%
-
-
?
(E)-2-methyl-2-butenoate + NADH
2-methylbutanoate + NAD+
-
-
-
-
?
(E)-2-methyl-2-butenoate + NADH
2-methylbutanoate + NAD+
-
-
-
-
?
(E)-2-methyl-2-butenoate + NADH
2-methylbutanoate + NAD+
-
-
-
?
(E)-2-methylbutenoate + NADH
(R)-2-methylbutanoate + NAD+
-
-
-
?
(E)-2-methylbutenoate + NADH
(R)-2-methylbutanoate + NAD+
-
-
-
?
(E)-2-methylbutenoate + NADH
(R)-2-methylbutanoate + NAD+
-
-
-
?
(E)-2-methylbutenoate + reduced methylviologen
(R)-2-methylbutanoate + methyl viologen
-
-
-
?
(E)-2-methylbutenoate + reduced methylviologen
(R)-2-methylbutanoate + methyl viologen
-
-
-
?
(E)-2-nitro-1-phenylpropene + NADH + H+
(S)-2-nitro-1-phenylpropane + NAD+
(E)-2-nitro-1-phenylpropene is reduced with a yield of 56% and enantioselectivity (16% ee for (S)-2-nitro-1-phenylpropane)
-
-
?
(E)-2-nitro-1-phenylpropene + NADH + H+
(S)-2-nitro-1-phenylpropane + NAD+
Clostridium sporogenes DSM 795
(E)-2-nitro-1-phenylpropene is reduced with a yield of 56% and enantioselectivity (16% ee for (S)-2-nitro-1-phenylpropane)
-
-
?
(E)-4-(2,4-dimethoxyphenyl)but-3-en-2-one + NAD+
4-(2,4-dimethoxyphenyl)butan-2-one + NADH + H+
-
-
-
-
?
(E)-4-(2,4-dimethoxyphenyl)but-3-en-2-one + NAD+
4-(2,4-dimethoxyphenyl)butan-2-one + NADH + H+
-
-
-
-
?
(E)-4-(4'-isopropylphenyl)but-3-en-2-one + NAD+
4-(4-isopropylphenyl)butan-2-one + NADH + H+
-
-
-
-
?
(E)-4-(4'-isopropylphenyl)but-3-en-2-one + NAD+
4-(4-isopropylphenyl)butan-2-one + NADH + H+
-
-
-
-
?
(E)-4-(4'-methoxyphenyl)but-3-en-2-one + NAD+
4-(4-methoxyphenyl)butan-2-one + NADH + H+
-
-
-
-
?
(E)-4-(4'-methoxyphenyl)but-3-en-2-one + NAD+
4-(4-methoxyphenyl)butan-2-one + NADH + H+