Information on EC 1.3.1.31 - 2-enoate reductase

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

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EC NUMBER
COMMENTARY hide
1.3.1.31
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RECOMMENDED NAME
GeneOntology No.
2-enoate reductase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
butanoate + NAD+ = but-2-enoate + NADH + H+
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dehydrogenation
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oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Phenylalanine metabolism
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Microbial metabolism in diverse environments
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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 hide
70712-51-5
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
chicory
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Manually annotated by BRENDA team
strain ATCC 8585D-5
UniProt
Manually annotated by BRENDA team
no activity in Clostridium butyricum
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Manually annotated by BRENDA team
no activity in Clostridium pasteurianum
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Manually annotated by BRENDA team
no activity in Clostridium propionicum
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Manually annotated by BRENDA team
subspecies Photorhabdus luminescens laumondii
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Manually annotated by BRENDA team
various red yeasts
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
strain ATCC 43970
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Manually annotated by BRENDA team
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-carvone + NADPH
?
show the reaction diagram
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biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 100%, ee: 97%
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?
(+)-costunolide + NADPH
11(S),13-dihydrocostunolide + NADP+
show the reaction diagram
(-)-carvone + NADPH
?
show the reaction diagram
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biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 100%, ee: 95%
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?
(1-nitroprop-1-en-2-yl)benzene + NADP+
?
show the reaction diagram
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?
(1-nitroprop-1-en-2-yl)benzene + NADP+
[(2R)-1-nitropropan-2-yl]benzene + NADPH + H+
show the reaction diagram
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product of isoform OPR1
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?
(1-nitroprop-1-en-2-yl)benzene + NADP+
[(2S)-1-nitropropan-2-yl]benzene + NADPH + H+
show the reaction diagram
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product of isoform OPR3
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?
(1-nitroprop-1-en-2-yl)benzene + NADP+
[(2S)-2-methyl-3-nitropropyl]benzene + NADPH + H+
show the reaction diagram
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?
(2E)-2-benzylidenecyclohexanone + NADPH
?
show the reaction diagram
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biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 92%, ee: 51%
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?
(2E)-2-benzylidenecyclopentanone + NADPH
?
show the reaction diagram
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biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 4%, ee: racemate
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?
(2E)-2-cyano-3-phenylprop-2-enoic acid + NADPH
2-cyano-3-phenylpropanoic acid + NADP+
show the reaction diagram
conversion rate measured using HPLC after 48 h. Conversion: 83%, ee: racemic
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?
(2E)-2-methyl-3-phenylacrylic acid + electron donor
2-methyl-3-phenylpropanoic acid + electron acceptor
show the reaction diagram
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?
(2E)-2-methyl-3-phenylbut-2-enoic acid + electron donor
2-methyl-3-phenylbutanoic acid + electron acceptor
show the reaction diagram
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?
(2E)-2-methylbut-2-enedioic acid + electron donor
2-methylbutanedioic aicd + electron acceptor
show the reaction diagram
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?
(2E)-2-methylpent-2-enal + NADH + H+
(2R)-2-methylpentanal + NAD+
show the reaction diagram
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?
(2E)-3,7-dimethylocta-2,6-dienal + NADH + H+
3,7-dimethyloct-6-enal + NAD+
show the reaction diagram
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?
(2E)-3-phenylacrylic acid + electron donor
3-phenylpropanoic acid + electron acceptor
show the reaction diagram
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?
(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
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?
(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
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?
(2E,4E)-2,3,5,8-tetramethylnona-2,4,7-trienoic acid + electron donor
? + electron acceptor
show the reaction diagram
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?
(2E,4E)-2,3-dimethylhexa-2,4-dienoic acid + electron donor
? + electron acceptor
show the reaction diagram
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?
(2E,6Z)-nona-2,6-dienal + NADH + H+
?
show the reaction diagram
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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+
show the reaction diagram
conversion rate measured using HPLC after 48 h. Conversion: 80%, ee: 94% (R)
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(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+
show the reaction diagram
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?
(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+
show the reaction diagram
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?
(E)-(2-nitroprop-1-en-1-yl)benzene + NADP+
?
show the reaction diagram
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?
(E)-(2-nitroprop-1-en-1-yl)benzene + NADP+
[(3S)-3-nitrobutyl]benzene + NADPH + H+
show the reaction diagram
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?
(E)-2,5-dimethoxycinnamate + NADH
3-(2,5-dimethoxyphenyl)propionate + NAD+
show the reaction diagram
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?
(E)-2-butenoate + NADH
butanoate + NAD+
show the reaction diagram
(E)-2-decenal + NADH + H+
decanal + NAD+
show the reaction diagram
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relative activity: 90%
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?
(E)-2-hexen-1-al + NADH + H+
hexanal + NAD+
show the reaction diagram
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relative activity: 100%
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?
(E)-2-hexenal + NADPH
hexanal + NADP+
show the reaction diagram
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relative activity: 100%
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?
(E)-2-methyl-2-butenal + NADH + H+
2-methylbutanal + NADH
show the reaction diagram
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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 + ?
show the reaction diagram
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?
(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
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?
(E)-2-methylbutenoate + NADH
(R)-2-methylbutanoate + NAD+
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
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relative activity: 57%
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?
(E)-2-octenal + NADH + H+
octanal + NAD+
show the reaction diagram
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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+
show the reaction diagram
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18% of the activity with butenoate
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?
(E)-2-pentenal + NADH + H+
2-pentanone + NAD+
show the reaction diagram
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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+
show the reaction diagram
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27% of the activity with butenoate
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?
(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
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relative activity: 36.6%
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?
(E)-3-nonen-2-one + NADPH
nonan-2-one + NADP+
show the reaction diagram
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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+
show the reaction diagram
(E)-4-(4'-isopropylphenyl)but-3-en-2-one + NAD+
4-(4-isopropylphenyl)butan-2-one + NADH + H+
show the reaction diagram
(E)-4-(4'-methoxyphenyl)but-3-en-2-one + NAD+
4-(4-methoxyphenyl)butan-2-one + NADH + H+
show the reaction diagram
(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+
show the reaction diagram
(E)-4-methyl-2-pentenoate + NADH
4-methylpentanoate + NAD+
show the reaction diagram
(E)-4-phenylbut-3-ene-2-one + NAD+
4-phenylbutan-2-one + NADH + H+
show the reaction diagram
(E)-cinnamate + NADH
phenylpropionate + NAD+
show the reaction diagram
(E)-ethyl 2-methyl-4-oxopent-2-enoate + NADP+
?
show the reaction diagram
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?
(E)-ethyl 2-methyl-4-oxopent-2-enoate + NADP+
ethyl (2R)-2-methyl-4-oxopentanoate + NADPH + H+
show the reaction diagram
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?
(E)-geraniate + NADH
?
show the reaction diagram
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?
(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
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?
(R)-(-)-carvone + NADH + H+
?
show the reaction diagram
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relative activity: 70%
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?
(R)-carvone + NADPH
2-methyl-5-(1-methylethenyl)cyclohexanone + NADP+
show the reaction diagram
(R,S)-1-methyl-3-phenylallenecarboxylate + NADH
? + NAD+
show the reaction diagram
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?
(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
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?
(Z)-2-chloro-3-(p-chlorophenyl)acrylate + NADH
2-chloro-3-(4-chlorophenyl)propionate + NAD+
show the reaction diagram
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?
(Z)-2-fluorocinnamate + NADH
3-(2-fluorophenyl)propionate + NAD+
show the reaction diagram
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?
(Z)-3-chlorocinnamate + NADH
3-(3-chlorophenyl)propionate + NAD+
show the reaction diagram
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?
(Z)-3-cyano-3-phenyl-propenoic acid + NADPH + H+
(R)-3-cyano-3-phenylpropanoic acid + NADP+
show the reaction diagram
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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?
(Z)-3-methylpentenoate + NADH
3-methylpentanoate + NAD+
show the reaction diagram
(Z)-geraniate + NADH
?
show the reaction diagram
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?
1,3-dimethyl-1H-pyrrole-2,5-dione + NADPH
?
show the reaction diagram
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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
?
show the reaction diagram
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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
?
show the reaction diagram
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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
?
show the reaction diagram
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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+
show the reaction diagram
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?
1-benzyl-3-methyl-1H-pyrrole-2,5-dione + NADH + H+
(3R)-1-benzyl-3-methylpyrrolidine-2,5-dione + NAD+
show the reaction diagram
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?
1-butyl-3-methyl-1H-pyrrole-2,5-dione + NADPH
?
show the reaction diagram
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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-ethyl-3-methyl-1H-pyrrole-2,5-dione + NADPH
?
show the reaction diagram
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biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 99%
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?
12-phenyldodec-2-enoic acid + electron donor
12-phenyldodecanoic acid + electron acceptor
show the reaction diagram
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-
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?
2,3-dimethylmaleimide + NADH
trans-dimethylsuccinimide + NAD+
show the reaction diagram
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?
2,6,6-trimethyl-2-cyclohexen-1,4-dione + NADPH
?
show the reaction diagram
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relative activity: 103%
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?
2,6,6-trimethylcyclohex-2-ene-1,4-dione + NADH + H+
(6R)-2,2,6-trimethylcyclohexane-1,4-dione + NAD+
show the reaction diagram
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?
2-cyclohexen-1-one + NADH
2-cyclohexanone + NAD+
show the reaction diagram
2-cyclohexen-1-one + NADH + H+
2-cyclohexanone + NAD+
show the reaction diagram
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-
-
-
?
2-cyclohexen-1-one + NADH + H+
cyclohexanone + NAD+
show the reaction diagram
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relative activity: 830%
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?
2-cyclohexen-1-one + NADPH
?
show the reaction diagram
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relative activity: 56.7%
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?
2-hydroxycyclopent-2-en-1-one + NADH + H+
(2S)-2-hydroxycyclopentan-1-one + NAD+
show the reaction diagram
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?
2-isopropyl-5-methyl-2-hexenal + NADH + H+
2-isopropyl-5-methylhexanal + NAD+
show the reaction diagram
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relative activity: 15.5%
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?
2-methyl-2-butenoate + NADH
2-methylbutanoate + NAD+
show the reaction diagram
2-methyl-2-cyclopenten-1-one + NADH + H+
?
show the reaction diagram
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relative activity: 62.7%
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?
2-methyl-N-phenylmaleimide + NADH + H+
(3R)-3-methyl-1-phenylpyrrolidine-2,5-dione + NAD+
show the reaction diagram
2-methyl-N-phenylmaleimide + NADPH
(3R)-3-methyl-1-phenylpyrrolidine-2,5-dione + NADP+
show the reaction diagram
2-methylbutenoate + NADH
2-methylbutanoate + NAD+
show the reaction diagram
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-
-
-
?
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%
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?
2-methylcyclopenten-1-one + NADPH
?
show the reaction diagram
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relative activity: 12.4%
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?
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%
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-
?
3-methyl-1-phenyl-1H-pyrrole-2,5-dione + NADPH
(R)-N-phenyl-2-methylsuccinimide + NADP+
show the reaction diagram
conversion rate measured using HPLC after 48 h. Conversion: 99%, ee: 99% (R)
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-
?
3-methyl-1-propyl-1H-pyrrole-2,5-dione + NADPH
?
show the reaction diagram
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biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 99%
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-
?
3-methyl-2-butenal + NADPH
3-methylbutanal + NADP+
show the reaction diagram
3-methyl-2-cyclopentenone + NADH + H+
?
show the reaction diagram
-
relative activity: 31%
-
-
?
3-methylpentenoate + NADH
3-methylpentanoate + NAD+
show the reaction diagram
4-(1,3-benzodioxol-5-yl)butan-2-one + NAD+
(S)-4-(1,3-benzodioxol-5-yl)butan-2-ol + NADH + H+
show the reaction diagram
-
-
-
-
?
4-coumaric acid + NAD+
3-(4-hydroxyphenyl)propionic acid + NADH + H+
show the reaction diagram
-
-
-
-
?
4-phenylbutan-2-one + NAD+
(S)-4-phenylbutan-2-ol + NADH + H+
show the reaction diagram
-
-
-
-
?
5-benzylidenethiazolidine-2,4-dione + NADH
(5R)-5-benzyl-1,3-thiazolidine-2,4-dione + NAD+
show the reaction diagram
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
butenoate + NADH
butanoate + NAD+
show the reaction diagram
butenoate + reduced methyl viologen
butanoate + methyl viologen
show the reaction diagram
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-
-
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chalcone + NAD+
dihydrochalcone + NADH + H+
show the reaction diagram
-
-
-
-
?
chloroacrylic acid + NADPH
(S)-2-chloropropionic acid + NADP+
show the reaction diagram
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-
-
-
?
cinnamaldehyde + NADPH
?
show the reaction diagram
cinnamate + NADH
phenylpropionate + NAD+
show the reaction diagram
cinnamic acid + NAD+
3-phenylpropionic acid + NADH + H+
show the reaction diagram
-
-
-
-
?
citraconic anhydride + NADH
?
show the reaction diagram
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-
-
-
?
citral + NADPH
3-phenylpropanal + NADP+
show the reaction diagram
citral + NADPH
?
show the reaction diagram
-
relative activity: 34%
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-
?
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%
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-
?
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
ethyl (2R)-3-nitro-2-phenylpropanoate + NADP+
show the reaction diagram
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
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
maleic anhydride + NADPH
dihydrofuran-2,5-dione + NADP+
show the reaction diagram
maleimide + NADH
pyrrolidine-2,5-dione + NADH
show the reaction diagram
methyl 2-phenylacrylate + NADP+
?
show the reaction diagram
-
-
-
-
?
methyl 2-phenylacrylate + NADP+
methyl (2R)-2-methyl-3-phenylpropanoate + NADPH + H+
show the reaction diagram
-
-
-
-
?
monomethyl fumarate + NADH
4-methoxy-4-oxobutanoate + NAD+
show the reaction diagram
-
-
-
-
?
N-ethylmaleimide + NADPH
N-ethylpyrrolidine-2,5-dione + NADH
show the reaction diagram
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
[(1E)-1-nitroprop-1-en-2-yl]benzene + NADPH
(S)-1-nitro-2-phenylpropane + NADP+
show the reaction diagram
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
conversion rate measured using HPLC after 48 h. Conversion: 60%, ee: racemic
-
-
?
additional information
?
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
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
-
-
?
chalcone + NAD+
dihydrochalcone + NADH + H+
show the reaction diagram
-
V9P074
-
-
-
?
additional information
?
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NAD(P)H
NADP+
NADPH
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
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 30°C
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
4-phenylbutanoate
Aliphatic carboxylates
-
-
aminobenzotriazole
-
slight inhibition
Benzoate
dicoumarol
dimethyl (2E)-2-methylbut-2-enedioate
-
-
dimethyl (2R)-2-methylbutanedioate
-
-
dimethyl (2S)-2-methylbutanedioate
-
-
dimethyl (2Z)-2-methylbut-2-enedioate
-
-
dimethyl 2-methylidenebutanedioate
-
-
fumarate
Mersalyl
-
1 mM, complete inhibition
methyl viologen
-
-
Metyrapone
-
slight inhibition
morin
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
reduced methyl viologen
-
-
additional information
-
not inhibited by 2-cyclohexanone
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
argon
-
34% activation
clotrimazole
-
slight activation
CO
-
atmosphere of 80% v/v with 20% v/v O2, 40% activation
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
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, 37°C
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, 30°C
0.0014
2-methyl-N-phenylmaleimide
pH 7.5, 30°C
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
-
-
1.5
butenoate
-
-
0.013 - 0.02
cinnamate
0.012 - 0.034
NADH
0.0854 - 1.24
NADPH
1.4
oct-2-en-4-ynoic acid
-
-
0.4
reduced methyl viologen
-
-
additional information
additional information
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
8400
2-cyclohexen-1-one
-
pH 7.0, 30°C
5.9
2-methyl-N-phenylmaleimide
pH 7.5, 30°C
38.6 - 3200
NADH
1.97 - 19.2
NADPH
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4.4
2-methyl-N-phenylmaleimide
pH 7.5, 30°C
2000
NADH
pH 7.5, 30°C
220
NADPH
pH 7.5, 30°C
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
20
methyl viologen
-
-
30
phenyl propionate
-
-
10
reduced methyl viologen
-
-
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2.46
highest specific activity with 10 mM N-ethylmaleimide in 200 mM sodium phosphate, at pH 7.5, 0.2 mM NADPH, at 25°C
15.81
-
highest specific activity with 10 mM maleimide in 200 mM sodium phosphate, at pH 7.5, 0.2 mM NADPH, at 25°C
20
-
(E)-2-methylbutenoate
25.82
highest specific activity with 10 mM maleimide in 200 mM sodium phosphate, at pH 7.5, 0.2 mM NADPH, at 25°C
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5
-
optimal activity in TEA buffer
7.5
highest activity using Tris-HCl
8
-
assay at
additional information
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
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
conversion rate drops to 20% at pH 6.0
7
highest conversion rate 54%, pH optimum
8
48% conversion rate
8 - 9
-
optimal pH range
9
only 30% of highest activity at pH 9
additional information
no activity at pH 11
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
28
-
assay at
35
optimal temperature in potassium phosphate buffer
45
-
optimal activity
53
-
only 25% residual activity
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20
about 40% of maximal activity maintained
45
about 40% of maximal activity maintained
50 - 55
-
temp. optimum
55
no activity beyond 55°C
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
39240
-
calculated from cDNA
40600
calculated from cDNA
42300
-
calculated from cDNA
42500
-
x * 42500, SDS-PAGE
44000
-
SDS-PAGE
45000
SDS-PAGE
46800
-
SDS-PAGE
75000
-
-
78000
-
6 * 78000, SDS-PAGE
170000
-
gel filtration
450000
-
gel filtration
600000
O52935;
gel filtration
800000
-
gel filtration
940000
-
equilibrium ultracentrifugation
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dodecamer
-
12 * 70000, SDS-PAGE; 12 * 73000, equilibrium sedimentation in guanidine hydrochloride
hexamer
-
6 * 78000, SDS-PAGE
tetramer
-
4 * 42300, gel filtration
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 9.5
-
the activity drops off sharply between pH 5-6 and pH 8.5-9.5
684248
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4 - 30
-
enzyme stable over 24 h
30
half-life of inactivation: 64.8 h
30 - 45
55
-
20 min, stable
59
-
midpoint thermal inactivation
65
-
no activity after 1 h
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GENERAL STABILITY
ORGANISM
UNIPROT
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
-
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OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
relatively stable in presence of oxygen, 50% loss of activity after 30 h
-
390672
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-18°C, pH 7, buffer containing 10 mM phosphate and 0.1 M KCl, formation of a dissociation product sedimenting at about 10 S
-
-20°C, phosphate buffer, pH 7.0, containing (E)-2-methyl-2-butenoate, EDTA, sucrose and 2-mercaptoethanol, repeatedly thawed and frozen, 50% loss of activity
-
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Ni-NTA column chromatography
-
Ni2+-NTA bead chromatography
recombinant enzyme
O52935;
using affinity chromatography
using ammonium sulfate precipitation and treatment in an acidic buffer
-
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed as a His-tagged fusion protein in Escherichia coli
-
expressed in Escherichia coli
expressed in Escherichia coli BL21
-
expressed in Escherichia coli BL21 Star(DE3) cells
-
expressed in Escherichia coli BL21(DE3)
expressed in Escherichia coli BL21(DE3) cells
-
expressed in Escherichia coli growing under anaerobic conditions
O52935;
expressed in Escherichia coli Rosetta (DE3) cells
-
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Renatured/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
using Ni-NTA chromatography
-
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Show AA Sequence (121 entries)
Please use the Sequence Search for a specific query.
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LINKS TO OTHER DATABASES (specific for EC-Number 1.3.1.31)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)