Information on EC 1.3.1.31 - 2-enoate reductase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY
1.3.1.31
-
RECOMMENDED NAME
GeneOntology No.
2-enoate reductase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
butanoate + NAD+ = but-2-enoate + NADH + H+
show the reaction diagram
-
-
-
-
butanoate + NAD+ = but-2-enoate + NADH + H+
show the reaction diagram
enzyme kinetics in reversed micelles; ping-pong mechanism in aqueous solution
-
butanoate + NAD+ = but-2-enoate + NADH + H+
show the reaction diagram
bi bi ping pong mechanism
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
dehydrogenation
-
-
-
-
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
Microbial metabolism in diverse environments
-
Phenylalanine metabolism
-
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.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Achr-OYE3
I3V5V5
-
Achr-OYE4
I3V5V6
-
Achr-OYE4
I3V5V6
-
-
acylate:NAD+ DELTA2 oxidoreductase
-
-
-
-
enoate reductase
-
-
-
-
enoate reductase
-
-
enoate reductase
I3V5V5
-
enoate reductase
I3V5V6
-
enoate reductase
I3V5V6
-
-
enoate reductase
-
-
enoate reductase
-
-
enoate reductase
-
-
enoate reductase
P40952
-
enoate reductase
-
-
enoate reductase
-
-
enoate reductase
-
-
enoate reductase
Q9R9V9
-
enoate reductase
-
-
enoate reductase
-
-
enoate reductase
-
-
NADPH dehydrogenase 1
P40952
-
old yellow enzyme
P40952
-
old yellow enzyme
Q9R9V9
-
old yellow enzyme
-
-
reductase, 2-enoate
-
-
-
-
XenA
Q9R9V9
xenobiotic reductase A showing enoate reductase activity toward 2-cyclohexen-1-one
yellow enzyme
-
-
CAS REGISTRY NUMBER
COMMENTARY
70712-51-5
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
Clostridium difficile
-
-
-
Manually annotated by BRENDA team
strain ATCC 8585D-5
UniProt
Manually annotated by BRENDA team
no activity in Clostridium butyricum
-
-
-
Manually annotated by BRENDA team
no activity in Clostridium pasteurianum
-
-
-
Manually annotated by BRENDA team
no activity in Clostridium propionicum
-
-
-
Manually annotated by BRENDA team
xenobiotic reductase A showing enoate reductase activity
UniProt
Manually annotated by BRENDA team
various red yeasts
-
-
Manually annotated by BRENDA team
Rhodotorula sp.
-
-
-
Manually annotated by BRENDA team
strain ATCC 43970
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-carvone + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 100%, ee: 97%
-
-
?
(+)-costunolide + NADPH
11(S),13-dihydrocostunolide + NADP+
show the reaction diagram
-
-, part of the metabolization of (+)-costunolide to leucodin, overview
-
-
?
(-)-carvone + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 100%, ee: 95%
-
-
?
(2E)-2-benzylidenecyclohexanone + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 92%, ee: 51%
-
-
?
(2E)-2-benzylidenecyclopentanone + NADPH
?
show the reaction diagram
-
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+
show the reaction diagram
I3V5V5
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
show the reaction diagram
-
-
-
-
?
(2E)-2-methyl-3-phenylbut-2-enoic acid + electron donor
2-methyl-3-phenylbutanoic acid + electron acceptor
show the reaction diagram
-
-
-
-
?
(2E)-2-methylbut-2-enedioic acid + electron donor
2-methylbutanedioic aicd + electron acceptor
show the reaction diagram
-
-
-
-
?
(2E)-3-phenylacrylic acid + electron donor
3-phenylpropanoic acid + electron acceptor
show the reaction diagram
-
-
-
-
?
(2E)-4-methoxy-2-methyl-4-oxobut-2-enoic acid + electron donor
4-methoxy-2-methyl-4-oxobutanoic acid + electron acceptor
show the reaction diagram
-
-
-
-
?
(2E)-4-methoxy-3-methyl-4-oxobut-2-enoic acid + electron donor
4-methoxy-3-methyl-4-oxobutanoic acid + electron acceptor
show the reaction diagram
-
-
-
-
?
(2E,4E)-2,3,5,8-tetramethylnona-2,4,7-trienoic acid + electron donor
? + electron acceptor
show the reaction diagram
-
-
-
-
?
(2E,4E)-2,3-dimethylhexa-2,4-dienoic acid + electron donor
? + electron acceptor
show the reaction diagram
-
-
-
-
?
(2Z)-3-(4-chlorophenyl)-3-cyanoprop-2-enoic acid + NADPH
(R)-3-(4-chlorophenyl)-3-cyano-propanoic acid + NADP+
show the reaction diagram
I3V5V5
conversion rate measured using HPLC after 48 h. Conversion: 80%, ee: 94% (R)
-
-
-
(E)-2,5-dimethoxycinnamate + NADH
3-(2,5-dimethoxyphenyl)propionate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-2,cis-6-nonadienal + NADH + H+
?
show the reaction diagram
-
relative activity: 62.7%
-
-
?
(E)-2-butenoate + NADH
butanoate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-2-butenoate + NADH
butanoate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-2-decenal + NADH + H+
decanal + NAD+
show the reaction diagram
-
relative activity: 90%
-
-
?
(E)-2-hexen-1-al + NADH+ H+
hexanal + NAD+
show the reaction diagram
-
relative activity: 100%
-
-
?
(E)-2-hexenal + NADPH
hexanal + NADP+
show the reaction diagram
-
relative activity: 100%
-
-
?
(E)-2-methyl-2-butenal + NADH + H+
2-methylbutanal + NADH
show the reaction diagram
-
relative activity: 59.2%
-
-
?
(E)-2-methyl-2-butenoate + 4,5-dihydroxyanthraquinone-2-carboxylic acid
2-methylbutanoate + ?
show the reaction diagram
-
-
-
-
?
(E)-2-methyl-2-butenoate + NADH
2-methylbutanoate + NAD+
show the reaction diagram
-
-
-
?
(E)-2-methyl-2-butenoate + NADH
2-methylbutanoate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-2-methyl-2-butenoate + NADH
2-methylbutanoate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-2-methyl-2-butenoate + NADH
2-methylbutanoate + NAD+
show the reaction diagram
-
-
-
?
(E)-2-methyl-2-butenoate + NADH
2-methylbutanoate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-2-methyl-3-phenyl-2-propenoate + reduced methyl viologen
(R)-2-methyl-3-phenyl-2-propanoate + methyl viologen
show the reaction diagram
-
-
-
?
(E)-2-methylbutenoate + NADH
(R)-2-methylbutanoate + NAD+
show the reaction diagram
O52935
-
-
-
?
(E)-2-methylbutenoate + NADH
(R)-2-methylbutanoate + NAD+
show the reaction diagram
-
-
-
?
(E)-2-methylbutenoate + NADH
(R)-2-methylbutanoate + NAD+
show the reaction diagram
O52933
-
-
-
?
(E)-2-methylbutenoate + reduced methylviologen
(R)-2-methylbutanoate + methyl viologen
show the reaction diagram
-
-
-
?
(E)-2-methylbutenoate + reduced methylviologen
(R)-2-methylbutanoate + methyl viologen
show the reaction diagram
-
-
-
?
(E)-2-nonenal + NADH + H+
nonanal + NAD+
show the reaction diagram
-
relative activity: 57%
-
-
?
(E)-2-octenal + NADH + H+
octanal + NAD+
show the reaction diagram
-
relative activity: 75.4%
-
-
?
(E)-2-oxo-4-phenyl-3-butenoate + NADH
2-oxo-4-phenyl-3-butanoate + NAD+
show the reaction diagram
-
18% of the activity with butenoate
-
-
?
(E)-2-pentenal + NADH + H+
2-pentanone + NAD+
show the reaction diagram
-
relative activity: 45%
-
-
?
(E)-3-methyl-2-oxo-4-phenyl-3-butenoate + NADH
3-methyl-2-oxo-4-phenyl-3-butenoate + NAD+
show the reaction diagram
-
27% of the activity with butenoate
-
-
?
(E)-3-methylpentenoate + NADH
3-methylpentanoate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-3-nonen-2-one + NADH + H+
nonan-2-one + NAD+
show the reaction diagram
-
relative activity: 36.6%
-
-
?
(E)-3-nonen-2-one + NADPH
nonan-2-one + NADP+
show the reaction diagram
-
relative activity: 61.6%
-
-
?
(E)-4-methyl-2-pentenoate + NADH
4-methylpentanoate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-4-methyl-2-pentenoate + NADH
4-methylpentanoate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-4-methyl-2-pentenoate + NADH
4-methylpentanoate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-4-methyl-2-pentenoate + NADH
4-methylpentanoate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-4-methyl-2-pentenoate + NADH
4-methylpentanoate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-cinnamate + NADH
phenylpropionate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-cinnamate + NADH
phenylpropionate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-cinnamate + NADH
phenylpropionate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-geraniate + NADH
?
show the reaction diagram
-
-
-
-
?
(E)-o-hydroxycinnamate + NADH
3-(2-hydroxyphenyl)propionate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-p-(dimethylamino)cinnamate + NADH
3-(4-(dimethylamino)phenyl)propionate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-p-chlorocinnamate + NADH
3-(4-chlorophenyl)propionate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-p-methoxycinnamate + NADH
3-(4-methoxyphenyl)propionate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-p-nitrocinnamate + NADH
3-(4-nitrophenyl)propionate + NAD+
show the reaction diagram
-
-
-
-
?
(E,E)-2,4-hexadienoate + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
(R)-(-)-carvone + NADH + H+
?
show the reaction diagram
-
relative activity: 70%
-
-
?
(R)-carvone + NADPH
2-methyl-5-(1-methylethenyl)cyclohexanone + NADP+
show the reaction diagram
-
-
-
-
?
(R)-carvone + NADPH
2-methyl-5-(1-methylethenyl)cyclohexanone + NADP+
show the reaction diagram
P40952
-
-
-
?
(R)-carvone + NADPH
2-methyl-5-(1-methylethenyl)cyclohexanone + NADP+
show the reaction diagram
Q9R9V9
-
-
-
?
(R,S)-1-methyl-3-phenylallenecarboxylate + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
(Z)-2-(formylamino)cinnamate + NADH
3-(4-(formylamino)phenyl)propionate + NAD+
show the reaction diagram
-
-
-
-
?
(Z)-2-bromocinnamate + NADH
3-(2-bromophenyl)propionate + NAD+
show the reaction diagram
-
-
-
-
?
(Z)-2-chloro-3-(p-chlorophenyl)acrylate + NADH
2-chloro-3-(4-chlorophenyl)propionate + NAD+
show the reaction diagram
-
-
-
-
?
(Z)-2-fluorocinnamate + NADH
3-(2-fluorophenyl)propionate + NAD+
show the reaction diagram
-
-
-
-
?
(Z)-3-chlorocinnamate + NADH
3-(3-chlorophenyl)propionate + NAD+
show the reaction diagram
-
-
-
-
?
(Z)-3-cyano-3-phenyl-propenoic acid + NADPH + H+
(R)-3-cyano-3-phenylpropanoic acid + NADP+
show the reaction diagram
I3V5V5
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)
-
-
?
(Z)-3-methylpentenoate + NADH
3-methylpentanoate + NAD+
show the reaction diagram
-
-
-
-
?
(Z)-geraniate + NADH
?
show the reaction diagram
-
-
-
-
?
1,3-dimethyl-1H-pyrrole-2,5-dione + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 99%
-
-
?
1-(cyclohex-1-en-1-yl)ethanone + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 71%, ee: not applicable
-
-
?
1-(cyclopent-1-en-1-yl)ethanone + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 30%, ee: not applicable
-
-
?
1-(prop-2-en-1-yl)-1H-pyrrole-2,5-dione + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: not applicable
-
-
?
1-butyl-3-methyl-1H-pyrrole-2,5-dione + NADPH
?
show the reaction diagram
-
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
?
show the reaction diagram
-
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
show the reaction diagram
-
-
-
-
?
2,3-dimethylmaleimide + NADH
trans-dimethylsuccinimide + NAD+
show the reaction diagram
-
-
-
-
?
2,6,6-trimethyl-2-cyclohexen-1,4-dione + NADPH
?
show the reaction diagram
-
relative activity: 103%
-
-
?
2-cyclohexen-1-one + NADH
2-cyclohexanone + NAD+
show the reaction diagram
-
-
-
-
?
2-cyclohexen-1-one + NADH
2-cyclohexanone + NAD+
show the reaction diagram
-
-
-
-
?
2-cyclohexen-1-one + NADH
2-cyclohexanone + NAD+
show the reaction diagram
P40952
-
-
-
?
2-cyclohexen-1-one + NADH
2-cyclohexanone + NAD+
show the reaction diagram
Q9R9V9
-
-
-
?
2-cyclohexen-1-one + NADH + H+
cyclohexanone + NAD+
show the reaction diagram
-
relative activity: 830%
-
-
?
2-cyclohexen-1-one + NADH + H+
2-cyclohexanone + NAD+
show the reaction diagram
-
-
-
-
?
2-cyclohexen-1-one + NADPH
?
show the reaction diagram
-
relative activity: 56.7%
-
-
?
2-isopropyl-5-methyl-2-hexenal + NADH + H+
2-isopropyl-5-methylhexanal + NAD+
show the reaction diagram
-
relative activity: 15.5%
-
-
?
2-methyl-2-butenoate + NADH
2-methylbutanoate + NAD+
show the reaction diagram
-
-
-
-
?
2-methyl-2-cyclopenten-1-one + NADH + H+
?
show the reaction diagram
-
relative activity: 62.7%
-
-
?
2-methyl-N-phenylmaleimide + NADH + H+
(3R)-3-methyl-1-phenylpyrrolidine-2,5-dione + NAD+
show the reaction diagram
I3V5V6
-
-
-
?
2-methyl-N-phenylmaleimide + NADPH
(2R)-2-methyl-1-phenylpyrrolidine-2,5-dione + NAD+
show the reaction diagram
I3V5V6
-
-
-
?
2-methylbutenoate + NADH
2-methylbutanoate + NAD+
show the reaction diagram
-
-
-
-
?
2-methylcyclopent-2-enone + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 92%, ee: 52%
-
-
?
2-methylcyclopenten-1-one + NADPH
?
show the reaction diagram
-
relative activity: 12.4%
-
-
?
2-methylenesuccinic acid + NAD(P)H
(R)-2-methylsuccinic acid + NAD(P)+
show the reaction diagram
-
-
-
-
?
2-methylfumaric acid + NAD(P)H
2-methylsuccinic acid + NAD(P)+
show the reaction diagram
-
-
-
-
?
2-methylmaleic acid + NAD(P)H
(R)-2-methylsuccinic acid + NAD(P)+
show the reaction diagram
-
-
-
-
?
3-methyl-1-(prop-2-en-1-yl)-1H-pyrrole-2,5-dione + NADPH
?
show the reaction diagram
-
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+
show the reaction diagram
I3V5V5
conversion rate measured using HPLC after 48 h. Conversion: 99%, ee: 99% (R)
-
-
?
3-methyl-1-propyl-1H-pyrrole-2,5-dione + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 99%
-
-
?
3-methyl-2-butenal + NADPH
3-methylbutanal + NADP+
show the reaction diagram
-
-
-
-
?
3-methyl-2-butenal + NADPH
3-methylbutanal + NADP+
show the reaction diagram
P40952
-
-
-
?
3-methyl-2-butenal + NADPH
3-methylbutanal + NADP+
show the reaction diagram
Q9R9V9
-
-
-
?
3-methyl-2-cyclopentenone + NADH + H+
?
show the reaction diagram
-
relative activity: 31%
-
-
?
3-methylpentenoate + NADH
3-methylpentanoate + NAD+
show the reaction diagram
-
-
-
-
?
5-benzylidenethiazolidine-2,4-dione + NADH
(5R)-5-benzyl-1,3-thiazolidine-2,4-dione + NAD+
show the reaction diagram
Rhodotorula sp., Rhodosporidium
-
-
-
-
?
alpha-methylmaleimide + NADH
(R)-2-methylsuccinimide + NAD+
show the reaction diagram
-
-
-
-
?
bromomaleic anhydride + NADH + H+
?
show the reaction diagram
-
relative activity: 107%
-
-
?
but-3-en-2-one + NADPH
butan-2-one + NADP+
show the reaction diagram
-
-
-
-
?
but-3-en-2-one + NADPH
butan-2-one + NADP+
show the reaction diagram
P40952
-
-
-
?
but-3-en-2-one + NADPH
butan-2-one + NADP+
show the reaction diagram
Q9R9V9
-
-
-
?
butenoate + NADH
butanoate + NAD+
show the reaction diagram
-
-
-
-
?
butenoate + NADH
butanoate + NAD+
show the reaction diagram
O52935
-
-
-
?
butenoate + NADH
butanoate + NAD+
show the reaction diagram
-
-
-
-
?
butenoate + NADH
butanoate + NAD+
show the reaction diagram
-
-
-
-
?
butenoate + NADH
butanoate + NAD+
show the reaction diagram
-
-
-
-
?
butenoate + NADH
butanoate + NAD+
show the reaction diagram
-
-
-
-
?
butenoate + NADH
butanoate + NAD+
show the reaction diagram
-
-
-
-
?
butenoate + NADH
butanoate + NAD+
show the reaction diagram
-
-
-
-
?
butenoate + NADH
butanoate + NAD+
show the reaction diagram
-
-
-
?
butenoate + NADH
butanoate + NAD+
show the reaction diagram
-
-
-
-
?
butenoate + NADH
butanoate + NAD+
show the reaction diagram
O52933
-
-
-
?
butenoate + NADH
butanoate + NAD+
show the reaction diagram
-
reverse reaction is energetically extremely unfavorable
-
-
?
butenoate + reduced methyl viologen
butanoate + methyl viologen
show the reaction diagram
-
-
-
-
-
chloroacrylic acid + NADPH
(S)-2-chloropropionic acid + NADP+
show the reaction diagram
-
-
-
-
?
cinnamaldehyde + NADPH
?
show the reaction diagram
-
-
-
-
?
cinnamaldehyde + NADPH
?
show the reaction diagram
P40952
-
-
-
?
cinnamaldehyde + NADPH
?
show the reaction diagram
Q9R9V9
-
-
-
?
cinnamate + NADH
phenylpropionate + NAD+
show the reaction diagram
-
-
-
-
?
cinnamate + NADH
phenylpropionate + NAD+
show the reaction diagram
-
-
-
-
-
cinnamate + NADH
phenylpropionate + NAD+
show the reaction diagram
-
-
-
-
?
cinnamate + NADH
phenylpropionate + NAD+
show the reaction diagram
-
-
-
-
?
citraconic anhydride + NADH
?
show the reaction diagram
-
-
-
-
?
citral + NADPH
3-phenylpropanal + NADP+
show the reaction diagram
-
-
-
-
?
citral + NADPH
3-phenylpropanal + NADP+
show the reaction diagram
P40952
-
-
-
?
citral + NADPH
3-phenylpropanal + NADP+
show the reaction diagram
Q9R9V9
-
-
-
?
citral + NADPH
?
show the reaction diagram
-
relative activity: 34%
-
-
?
diethyl (2Z)-2-methylbut-2-enedioate + NADPH
?
show the reaction diagram
-
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)+
show the reaction diagram
-
-
-
-
?
dimethyl (2Z)-2-methylbut-2-enedioate + NAD(P)H
dimethyl (2R)-2-methylbutanedioate + NAD(P)+
show the reaction diagram
-
-
-
-
?
dimethyl (2Z)-2-methylbut-2-enedioate + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 98%
-
-
?
dimethyl 2-methylidenebutanedioate + NAD(P)H
dimethyl (2R)-2-methylbutanedioate + NAD(P)+
show the reaction diagram
-
-
-
-
?
dimethyl 2-methylidenebutanedioate + NADPH
?
show the reaction diagram
-
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
(R)-ethyl-3-nitro-2-phenylpropanoate + NADP+
show the reaction diagram
I3V5V5
conversion rate measured using HPLC after 48 h. Conversion: 40%, ee: 45% (R)
-
-
?
ethyl 3-(tetrahydrofuran)propanoate + NADP+
? + NADPH
show the reaction diagram
-
-
-
-
?
ethyl 3-(tetrahydrofuran)propanoate + NADPH
? + NADP+
show the reaction diagram
P40952
-
-
-
?
ethyl 3-(tetrahydrofuran)propanoate + NADPH
? + NADP+
show the reaction diagram
Q9R9V9
-
-
-
?
hexa-2,4-dienoic acid + electron donor
? + electron acceptor
show the reaction diagram
-
-
-
-
?
indolylacrylate + NADH
indolepropionate + NAD+
show the reaction diagram
-
-
-
-
?
ketoisophorone + NAD(P)H
(6R)-levodione + NAD(P)+
show the reaction diagram
-
-
-
-
?
ketoisophorone + NADPH
(6R)-levodione
show the reaction diagram
-
-
-
-
?
ketoisophorone + NADPH
(6R)-levodione
show the reaction diagram
P40952
-
-
-
?
ketoisophorone + NADPH
(6R)-levodione
show the reaction diagram
Q9R9V9
-
-
-
?
maleic anhydride + NADPH
dihydrofuran-2,5-dione + NADP+
show the reaction diagram
-
-
-
-
?
maleic anhydride + NADPH
dihydrofuran-2,5-dione + NADP+
show the reaction diagram
P40952
-
-
-
?
maleic anhydride + NADPH
dihydrofuran-2,5-dione + NADP+
show the reaction diagram
Q9R9V9
-
-
-
?
maleimide + NADH
pyrrolidine-2,5-dione + NADH
show the reaction diagram
-
-
-
-
?
maleimide + NADH
pyrrolidine-2,5-dione + NADH
show the reaction diagram
P40952
-
-
-
?
maleimide + NADH
pyrrolidine-2,5-dione + NADH
show the reaction diagram
Q9R9V9
-
-
-
?
N-ethylmaleimide + NADPH
N-ethylpyrrolidine-2,5-dione + NADH
show the reaction diagram
-
-
-
-
?
N-ethylmaleimide + NADPH
N-ethylpyrrolidine-2,5-dione + NADH
show the reaction diagram
P40952
-
-
-
?
N-ethylmaleimide + NADPH
N-ethylpyrrolidine-2,5-dione + NADH
show the reaction diagram
Q9R9V9
-
-
-
?
oct-2-en-4-ynoic acid + electron donor
? + electron acceptor
show the reaction diagram
-
-
-
-
?
phenylmaleic anhydride + NADH + H+
?
show the reaction diagram
-
relative activity: 402%
-
-
?
trans,trans-2,4-hexadienal + NADPH
?
show the reaction diagram
-
-
-
-
?
trans,trans-2,4-hexadienal + NADPH
?
show the reaction diagram
P40952
-
-
-
?
trans,trans-2,4-hexadienal + NADPH
?
show the reaction diagram
Q9R9V9
-
-
-
?
[(1E)-1-nitroprop-1-en-2-yl]benzene + NADPH
(S)-1-nitro-2-phenylpropane + NADP+
show the reaction diagram
I3V5V5
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+
show the reaction diagram
I3V5V5
conversion rate measured using HPLC after 48 h. Conversion: 60%, ee: racemic
-
-
?
monomethyl fumarate + NADH
4-methoxy-4-oxobutanoate + NAD+
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
-
-
-
-
additional information
?
-
-
transhydrogenase activity: reduction of 3-acetylpyridine adenine dinucleotide by NADH
-
-
-
additional information
?
-
-
reduction of enoate is coupled to the formation of ATP
-
-
-
additional information
?
-
-
enzyme is involved in the reduction of allyl alcohols
-
-
-
additional information
?
-
-
activity reaches a maximum in cells of the stationary phase
-
-
-
additional information
?
-
-
enzyme may be part of the O2-dependent cytochrome P450-enzyme (+)-costunolide synthase, pathway, overview
-
-
-
additional information
?
-
-
NADPH does not react at all in the presence of 2-cyclohexen-1-one and rarely in presence of maleimide
-
-
-
additional information
?
-
P40952
NADPH does not react at all in the presence of 2-cyclohexen-1-one and rarely in presence of maleimide
-
-
-
additional information
?
-
Q9R9V9
NADPH does not react at all in the presence of 2-cyclohexen-1-one and rarely in presence of maleimide
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(+)-costunolide + NADPH
11(S),13-dihydrocostunolide + NADP+
show the reaction diagram
-
part of the metabolization of (+)-costunolide to leucodin, overview
-
-
?
additional information
?
-
-
-
-
-
-
additional information
?
-
-
enzyme is involved in the reduction of allyl alcohols
-
-
-
additional information
?
-
-
activity reaches a maximum in cells of the stationary phase
-
-
-
additional information
?
-
-
enzyme may be part of the O2-dependent cytochrome P450-enzyme (+)-costunolide synthase, pathway, overview
-
-
-
COFACTOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
FAD
-
contains 1 mol per mol of subunit
FAD
-
enzyme contains 1 mol of FAD per mol of subunit
FMN
-
contains 1 mol per mol of subunit
NADH
-
the enzyme splits off exclusively the (4S)-hydrogen
NADH
P40952
the enzymes shows very little or no activity with NADH
NADH
Q9R9V9
the enzymes shows very little or no activity with NADH
NADH
-
the enzymes shows very little or no activity with NADH
NADH
-
dependent on
NADH
Rhodosporidium, Rhodotorula sp.
-
-
NADH
I3V5V6
preferred cofactor
NADPH
-
dependent on, poor activity with NADH
NADPH
P40952
preferred cofactor
NADPH
Q9R9V9
preferred cofactor
NADPH
-
preferred cofactor
NADPH
-
dependent on
NADPH
-
NADPH is preferred, showing an 8fold higher specific activity
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Fe
-
iron-sulfur protein, contains 4.7 mol Fe per mol of subunit
Fe
-
iron-sulfur protein, contains 3.5-3.8 atoms of iron and 4.0 atoms of labile sulfur per subunit
Fe
-
presence of a [4Fe-4S]+2/+1 center, involvement of the iron-sulfur center in the enzyme mechanism
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
2-cyclohexen-1-one
-
the addition of 260 mM 2-cyclohexen-1-one leads to a more than 30fold decrease of the half-life at 30C
2-methylbutenoate
-
in all reversed micellar solutions inhibition by the enoate is observed at an overall concentration of 0.5-5 mM, implying that a concentration of substrate equal to the Km value in aqueous solution may already cause inhibition in reversed micelles
3-Phenylpropionate
-
inhibits reduction of (E)-2-methyl-2-butenoate
4-phenylbutanoate
-
inhibits reduction of (E)-2-methyl-2-butenoate
Aliphatic carboxylates
-
-
aminobenzotriazole
-
slight inhibition
Benzoate
-
inhibits reduction of (E)-2-methyl-2-butenoate
dicoumarol
-
blocks the NAD-binding domain
dimethyl (2E)-2-methylbut-2-enedioate
-
-
dimethyl (2R)-2-methylbutanedioate
-
-
dimethyl (2S)-2-methylbutanedioate
-
-
dimethyl (2Z)-2-methylbut-2-enedioate
-
-
dimethyl 2-methylidenebutanedioate
-
-
Mersalyl
-
1 mM, complete inhibition
morin
-
blocks the NAD-binding domain
NAD+
-
mixed-type inhibitor
O2
-
in the reduced state the enzyme is inactivated in 1-2 min, about 3 h after the removal of oxygen, the activity is partially restored
p-hydroxymercuribenzoate
-
0.1 mM, complete inhibition
phenyl propionate
-
-
phenylacetate
-
inhibits reduction of (E)-2-methyl-2-butenoate
reduced methyl viologen
-
-
Metyrapone
-
slight inhibition
additional information
-
not inhibited by 2-cyclohexanone
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
argon
-
34% activation
clotrimazole
-
slight activation
CO
-
atmosphere of 80% v/v with 20% v/v O2, 40% activation
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.029
-
(2E)-2-methyl-3-phenylacrylic acid
-
-
0.037
-
(2E)-2-methyl-3-phenylbut-2-enoic acid
-
-
7.4
-
(2E)-2-methylbut-2-enedioic acid
-
-
0.15
-
(2E)-3-phenylacrylic acid
-
-
0.8
-
(E)-2-butenoate
-
-
0.82
-
(E)-2-hexenal
-
pH 7.0, 37C
1.67
-
(E)-2-methyl-2-butenoate
-
-
0.014
-
(E)-geraniate
-
-
0.5
-
(Z)-2-bromocinnamate
-
-
-
0.1
-
(Z)-geraniate
-
-
0.01
-
12-phenyldodec-2-enoic acid
-
-
1.94
-
2-cyclohexen-1-one
-
pH 7.0, 30C
0.0014
-
2-methyl-N-phenylmaleimide
I3V5V6
pH 7.5, 30C
-
6
-
2-methylbutenoate
-
in 50 mM HEPES, pH 7.0, ionic strength 0.05 M
1.7
-
4-methoxy-2-methyl-4-oxobutanoic acid
-
-
16.2
-
4-methoxy-3-methyl-4-oxobutanoic acid
-
-
0.013
-
cinnamate
-
-
0.0191
-
NADH
I3V5V6
pH 7.5, 30C
0.02
-
NADH
-
in 50 mM HEPES, pH 7.0, ionic strength 0.05 M
0.034
-
NADH
-
pH 7.0, 30C
0.0854
-
NADPH
I3V5V6
pH 7.5, 30C
0.16
-
NADPH
-
pH 7.0, 37C
1.24
-
NADPH
-
at 25C and pH 7.5
1.4
-
oct-2-en-4-ynoic acid
-
-
0.4
-
reduced methyl viologen
-
-
0.02
-
cinnamate
-
-
additional information
-
additional information
-
-
-
additional information
-
additional information
-
-
-
additional information
-
additional information
-
Km-value for NADH is lower than 0.02 mM
-
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
8400
-
2-cyclohexen-1-one
-
pH 7.0, 30C
5.9
-
2-methyl-N-phenylmaleimide
I3V5V6
pH 7.5, 30C
-
38.6
-
NADH
I3V5V6
pH 7.5, 30C
3200
-
NADH
-
pH 7.0, 30C
1.97
-
NADPH
-
at 25C and pH 7.5
19.2
-
NADPH
I3V5V6
pH 7.5, 30C
kcat/KM VALUE [1/mMs-1]
kcat/KM VALUE [1/mMs-1] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
4.4
-
2-methyl-N-phenylmaleimide
I3V5V6
pH 7.5, 30C
0
2000
-
NADH
I3V5V6
pH 7.5, 30C
14331
220
-
NADPH
I3V5V6
pH 7.5, 30C
27498
Ki VALUE [mM]
Ki VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
20
-
methyl viologen
-
-
30
-
phenyl propionate
-
-
10
-
reduced methyl viologen
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
2.46
-
P40952
highest specific activity with 10 mM N-ethylmaleimide in 200 mM sodium phosphate, at pH 7.5, 0.2 mM NADPH, at 25C
15.81
-
-
highest specific activity with 10 mM maleimide in 200 mM sodium phosphate, at pH 7.5, 0.2 mM NADPH, at 25C
20
-
-
(E)-2-methylbutenoate
25.82
-
Q9R9V9
highest specific activity with 10 mM maleimide in 200 mM sodium phosphate, at pH 7.5, 0.2 mM NADPH, at 25C
additional information
-
-
design and application of sensitive enzyme immunoassays specific for clostridial enoate reductase
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5.5
-
-
optimal activity in TEA buffer
7
-
-
optimal activity incitrate-phosphate buffer
7.5
-
I3V5V6
highest activity using Tris-HCl
8
-
-
assay at
additional information
-
-
pH-optima for transhydrogenase activity
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
4.5
6.2
-
about 65% of maximal activity at pH 4.5 and at pH 6.2
5
9
O52935
active between pH 5.0 and pH 9.0
6
-
I3V5V5
conversion rate drops to 20% at pH 6.0
7
-
I3V5V5
highest conversion rate 54%, pH optimum
8
9
-
optimal pH range
8
-
I3V5V5
48% conversion rate
9
-
I3V5V6
only 30% of highest activity at pH 9
additional information
-
I3V5V6
no activity at pH 11
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
28
-
-
assay at
30
-
-
only 25% residual activity
30
-
I3V5V6
optimal temperature in Tris-HCl buffer
35
-
I3V5V6
optimal temperature in potassium phosphate buffer
37
-
-
assay at
45
-
-
optimal activity
53
-
-
only 25% residual activity
TEMPERATURE RANGE
TEMPERATURE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
20
-
I3V5V6
about 40% of maximal activity maintained
45
-
I3V5V6
about 40% of maximal activity maintained
50
55
-
temp. optimum
55
-
I3V5V6
no activity beyond 55C
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
39240
-
-
calculated from cDNA
40600
-
I3V5V6
calculated from cDNA
42300
-
-
calculated from cDNA
44000
-
-
SDS-PAGE
45000
-
I3V5V6
SDS-PAGE
46800
-
-
SDS-PAGE
170000
-
-
gel filtration
450000
-
-
gel filtration
600000
-
O52935
gel filtration
800000
-
-
gel filtration
940000
-
-
equilibrium ultracentrifugation
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
O52935
x * 73000, SDS-PAGE
dodecamer
-
12 * 70000, SDS-PAGE; 12 * 73000, equilibrium sedimentation in guanidine hydrochloride
hexamer
-
6 * 78000, SDS-PAGE
tetramer
-
4 * 42300, gel filtration
pH STABILITY
pH STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5
9.5
-
the activity drops off sharply between pH 5-6 and pH 8.5-9.5
TEMPERATURE STABILITY
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
4
30
-
enzyme stable over 24 h
30
45
P40952
KYE1 has a half-life of 1146 min at 30C, 210 min at 37C, and less than 5 min at 45C
30
45
Q9R9V9
XenA has a half-life of 600 min at 30C, 99 min at 37C, and less than 5 min at 45C
30
45
-
Yers-ER has a half-life of more than 2160 min at 30C, 1488 min at 37C, and 117 min at 45C
30
-
I3V5V6
half-life of inactivation: 64.8 h
55
-
-
20 min, stable
59
-
-
midpoint thermal inactivation
65
-
-
no activity after 1 h
GENERAL STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
enzyme immobilized in calcium alginate gel, used in operation for 2 weeks, half-life of about 200 h
-
half-life of 150 h during operation, in the immobilized form on filter paper. Half-life: 350 h, electrode immobilized enzyme
-
OXIDATION STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
relatively stable in presence of oxygen, 50% loss of activity after 30 h
-
390672
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
-20C, phosphate buffer, pH 7.0, containing (E)-2-methyl-2-butenoate, EDTA, sucrose and 2-mercaptoethanol, repeatedly thawed and frozen, 50% loss of activity
-
-18C, pH 7, buffer containing 10 mM phosphate and 0.1 M KCl, formation of a dissociation product sedimenting at about 10 S
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
using affinity chromatography
I3V5V6
Ni2+-NTA bead chromatography
P40952
using ammonium sulfate precipitation and treatment in an acidic buffer
-
recombinant enzyme
O52935
Ni2+-NTA bead chromatography
Q9R9V9
Ni2+-NTA bead chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expressed in Escherichia coli
-
expressed in Escherichia coli
-
expressed as a His-tagged fusion protein in Escherichia coli
-
expressed in Escherichia coli BL21(DE3)
P40952
expressed in Escherichia coli
-
expressed in Escherichia coli growing under anaerobic conditions
O52935
expressed in Escherichia coli BL21(DE3)
Q9R9V9
expressed in Escherichia coli BL21
-
expressed in Escherichia coli
-
expressed in Escherichia coli BL21(DE3)
-
Renatured/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
using Ni-NTA chromatography
-