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(4S)-3-[5-(4-fluorophenyl)-1,5-dioxopentyl]-4-phenyl-2-oxazolidinone + NADPH + H+
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one + NADP+
-
99.1% conversion
-
-
?
(R)-1-phenyl-1,2-ethanediol + NADH + H+
2-hydroxyacetophenone + NAD+
-
-
-
r
(R)-2-butanol + NADP+
2-butanone + NADPH + H+
(S)-2-butanol + NADP+
2-butanone + NADPH + H+
1,2-naphthoquinone + NADPH + H+
? + NADP+
-
-
-
?
1,4-benzoquinone + NADPH
?
-
-
-
-
?
1,4-benzoquinone + NADPH
? + NADP+
-
native and recombinant enzymes, low activity
-
-
?
1,4-naphthoquinone + NADPH + H+
?
-
-
-
-
?
1,4-naphthoquinone + NADPH + H+
? + NADP+
1-(3-methyl-1,4-dioxidoquinoxalin-2-yl)ethanone + NADPH + H+
1-(3-methyl-1,4-dioxidoquinoxalin-2-yl)ethanol + NADP+
1-(3-methyl-4-oxidoquinoxalin-2-yl)ethanone + NADPH + H+
1-(3-methyl-4-oxidoquinoxalin-2-yl)ethanol + NADP+
1-(3-nitrosophenyl)ethan-1-one + NADPH + H+
1-(3-nitrosophenyl)ethan-1-ol + NADP+
1-(4-chlorophenyl)ethan-1-one + NADPH + H+
1-(4-chlorophenyl)ethan-1-ol + NADP+
1-(4-chlorophenyl)ethanone + NADPH + H+
(S)-1-(4-chlorophenyl)ethanol + NADP+
1-(4-nitrosophenyl)ethan-1-one + NADPH + H+
1-(4-nitrosophenyl)ethan-1-ol + NADP+
1-acetonaphthone + NADPH
? + NADP+
1-acetonaphtone + NADPH + H+
? + NADP+
1-adamantyl methyl ketone + NADPH + H+
1-adamantyl methyl alcohol + NADP+
-
reduction of the sterically bulky ketone to the corresponding alcohol with excellent optical purity
-
-
?
1-butanal + NADPH
1-butanol + NADP+
-
-
-
-
?
1-butanal + NADPH + H+
1-butanol + NADP+
-
-
-
?
1-heptanal + NADPH
1-heptanol + NADP+
-
-
-
-
?
1-hexanal + NADPH
1-hexanol + NADP+
-
-
-
-
?
1-indanone + NADPH
1-indanol + NADP+
-
-
-
-
?
1-methylisatin + NADPH
?
Candida macedoniensis
-
-
-
-
?
1-nonanal + NADPH
1-nonanol + NADP+
-
-
-
-
?
1-pentanal + NADPH
1-pentanol + NADP+
-
-
-
-
?
1-phenyl-1,2-propandione + NADPH + H+
(R)-1-phenyl-2-hydroxy-1-propanone + NADP+
1-phenyl-1,2-propandione + NADPH + H+
(S)-1-phenyl-2-hydroxy-1-propanone + NADP+
1-phenyl-1,2-propanedione + NADPH
? + NADP+
-
recombinant enzyme
-
-
?
1-phenylethan-1-one + NADPH + H+
1-phenylethan-1-ol + NADP+
1-phenylethanone + NADPH + H+
(S)-1-phenylethanol + NADP+
1-phenylisatin + NADPH
? + NADP+
1-propanal + NADPH
1-propanol + NADP+
-
-
-
-
?
13,14-dihydro-15-ketoprostaglandin F2alpha + NADPH
13,14-dihydroprostaglandin F2alpha + NADP+
13-deoxydoxorubicin + NADPH + H+
?
an anthracyclin, formation of a 13-hydroxy-anthracyclin
-
-
?
16-ketoestrone + NADPH
? + NADP+
2 4-fluoroacetophenone + 2 NADPH + 2 H+
(1S)-1-(4-fluorophenyl)ethanol + (1R)-1-(4-fluorophenyl)ethanol + 2 NADP+
-
-
wild-type, (R)-configuration of product with 46% enantiomeric excess, mutant Q245H, (S)-configuration with 92%, mutant Q245P, with 90%, mutant Q245L, with 93% enantiomeric excess, respectively
-
?
2 ferricyanide + NADPH
2 ferrocyanide + NADP+ + H+
-
-
-
-
?
2'-fluoroacetophenone + NADPH + H+
? + NADP+
2'-methoxyacetophenone + NADPH + H+
1-(2-methoxyphenyl)ethanol + NADP+
-
reduction of the sterically bulky ketone to the corresponding alcohol with excellent optical purity
-
-
?
2,2,2-trifluoro-1-phenylethan-1-one + NADPH + H+
2,2,2-trifluoro-1-phenylethan-1-ol + NADP+
2,2,2-trifluoroacetophenone + NADPH + H+
(1S)-2,2,2-trifluoro-1-phenylethanol + NADP+
2,2,2-trifluoroacetophenone + NADPH + H+
(R)-2,2,2-trifluoro-1-phenylethanol + NADP+
2,2,2-trifluoroacetophenone + NADPH + H+
alpha-(trifluoromethyl)benzyl alcohol + NADP+
-
-
-
-
?
2,2-dimethylcyclohexanone-1,3-dione + NADPH + H+
(S)-3-hydroxy-2,2-dimethylcyclohexanone + NADP+
-
-
-
-
?
2,2-dimethylpropiophenone + NADPH + H+
2,2-dimethylpropiophenol + NADP+
-
-
over 90% chiral purity of the alcohol product
-
?
2,3-bornanedione + NADPH
?
-
-
-
-
?
2,3-butanediol + NADP+
acetoin + NADPH + H+
-
-
-
-
?
2,3-butanedione + NADPH
?
-
-
-
-
?
2,3-butanedione + NADPH
? + NADP+
2,3-butanedione + NADPH + H+
?
-
-
-
?
2,3-butanedione + NADPH + H+
? + NADP+
2,3-heptandione + NADPH + H+
? + NADP+
2,3-heptanedione + NADPH
? + NADP+
-
-
-
-
r
2,3-heptanedione + NADPH + H+
? + NADP+
18.8% of the activity with dihydroxyacetone
-
-
?
2,3-hexadione + NADPH
? + NADP+
-
recombinant enzyme
-
-
?
2,3-hexandione + NADPH + H+
? + NADP+
2,3-hexanedione + NADPH
? + NADP+
-
-
-
-
r
2,3-hexanedione + NADPH + H+
? + NADP+
2,3-pentanedione + NADPH + H+
(R)-2-hydroxy-pentane-3-one + NADP+
2,3-pentanedione + NADPH + H+
(S)-2-hydroxy-pentane-3-one + NADP+
2,3-pentanedione + NADPH + H+
? + NADP+
2,4-dichlorobenzaldehyde + NADPH + H+
2,4-dichlorobenzyl alcohol + NADP+
lowest activity
-
-
?
2,4-octanedione + NADPH + H+
(S)-2-hydroxy-4-octanone + NADP+
-
-
-
-
?
2,5-diketo-D-gluconate + NADPH + H+
? + NADP+
-
-
-
?
2-(3,4,6-tri-[3,4,5,6-tetrahydro])phthalimido-ethyl-3-oxobutanoate + NADPH + H+
ethyl (3R)-2-[(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)methyl]-3-hydroxybutanoate + NADP+
-
-
-
-
?
2-(3,5-difluoro)phthalimido-ethyl-3-oxobutanoate + NADPH + H+
ethyl (3R)-2-[(4,7-difluoro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-3-hydroxybutanoate + NADP+
-
-
-
-
?
2-(3-fluoro)phthalimido-ethyl-3-oxobutanoate + NADPH + H+
ethyl (3R)-2-[(4-fluoro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-3-hydroxybutanoate + NADP+
-
-
-
-
?
2-(3-fluoro)phthalimido-methyl-3-oxobutanoate + NADPH + H+
methyl (3R)-2-[(4-fluoro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-3-hydroxybutanoate + NADP+
-
-
-
-
?
2-(3-methoxy)phthalimido-ethyl-3-oxobutanoate + NADPH + H+
ethyl (3R)-3-hydroxy-2-[(4-methoxy-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]butanoate + NADP+
-
-
-
-
?
2-(4-fluoro)phthalimido-ethyl-3-oxobutanoate + NADPH + H+
ethyl (3R)-2-[(5-fluoro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-3-hydroxybutanoate + NADP+
-
-
-
-
?
2-(4-methyl)phthalimido-ethyl-3-oxobutanoate + NADPH + H+
ethyl (3R)-3-hydroxy-2-[(5-methyl-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]butanoate + NADP+
-
-
-
-
?
2-(4-methyl)phthalimido-methyl-3-oxobutanoate + NADPH + H+
methyl (3R)-3-hydroxy-2-[(5-methyl-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]butanoate + NADP+
-
-
-
-
?
2-(4-tert-butyl)phthalimido-ethyl-3-oxobutanoate + NADPH + H+
ethyl (3R)-2-[(5-tert-butyl-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-3-hydroxybutanoate + NADP+
-
-
-
-
?
2-benzoylpyridine + NADPH
(S)-alpha-phenyl-2-pyridylmethanol + NADP+
-
highly stereoselective reaction, native and recombinant enzymes, low activity
-
-
?
2-benzoylpyridine + NADPH
?
-
-
-
-
?
2-bromo-aceto-2-chlorophenone + NADPH
(R)-2-bromo-1-(2-chlorophenyl)ethanol + NADP+
-
stereospecific enzyme
product reacts spontaneously to the (R)-styrene oxide derivative in NaOH
-
?
2-bromo-aceto-3-chlorophenone + NADPH
(R)-2-bromo-1-(3-chlorophenyl)ethanol + NADP+
-
stereospecific enzyme
product reacts spontaneously to the (R)-styrene oxide derivative in NaOH
-
?
2-bromo-aceto-4-chlorophenone + NADPH
(R)-2-bromo-1-(4-chlorophenyl)ethanol + NADP+
-
stereospecific enzyme
product reacts spontaneously to the (R)-styrene oxide derivative in NaOH
-
?
2-bromo-acetophenone + NADPH
(R)-2-bromo-1-phenylethanol + NADP+
-
i.e. phenacyl bromide, stereospecific enzyme
product reacts spontaneously to the (R)-styrene oxide derivative in NaOH
-
?
2-bromobenzaldehyde + NADPH + H+
2-bromobenzyl alcohol + NADP+
-
-
-
?
2-butanol + NADP+
2-butanone + NADPH + H+
-
-
-
-
r
2-butanone + NADPH
2-butanol + NADP+
2-chloro-1-(3,4-dichlorophenyl)ethan-1-one + NADPH + H+
2-chloro-1-(3,4-dichlorophenyl)ethan-1-ol + NADP+
-
41% conversion after 24 h, 99% R-enantiomeric excess
-
-
?
2-chloro-aceto-3-chlorophenone + NADPH
(R)-2-chloro-1-(3-chlorophenyl)ethanol + NADP+
-
i.e. 3-chlorophenacyl chloride
product reacts spontaneously to the (R)-styrene oxide derivative in NaOH
-
?
2-chloroacetophenone + NADPH + H+
(R)-2-chloro-1-phenylethanol + NADP+
2-chloroacetophenone + NADPH + H+
(RS)-2-chloro-1-phenylethan-1-ol + NADP+
2-chlorobenzaldehyde + NADPH + H+
2-chlorobenzyl alcohol + NADP+
2-chlorobenzaldehyde + NADPH + H+
2-chlorobenzylalcohol + NADP+
-
-
-
-
?
2-cyanobenzaldehyde + NADPH + H+
2-cyanobenzyl alcohol + NADP+
-
-
-
?
2-fluorobenzaldehyde + NADPH + H+
2-fluorobenzyl alcohol + NADP+
-
-
-
?
2-halo-acetophenone + NADPH
(R)-2-halo-1-phenylethanol + NADP+
-
i.e. phenacyl halide, stereospecific enzyme
product reacts spontaneously to the (R)-styrene oxide derivative in NaOH
-
?
2-heptanone + NADPH
2-heptanol + NADP+
-
-
-
-
?
2-hydroxy-3-butanone + NADPH
2,3-dihydroxybutanol + NADP+
-
-
-
?
2-hydroxyacetophenone + NADH + H+
(S)-1-phenyl-1,2-ethanediol + NAD+
2-hydroxyacetophenone + NADPH + H+
(R)-1-phenyl-1,2-ethanediol + NADP+
2-hydroxyacetophenone + NADPH + H+
(RS)-1-phenyl-1,2-ethanediol + NADP+
2-hydroxyacetophenone + NADPH + H+
(S)-1-phenyl-1,2-ethanediol + NADP+
2-ketopantothenonitrile + NADPH
?
Candida macedoniensis
-
-
-
-
?
2-methyl-1,4-benzoquinone + NADPH
?
-
-
-
-
?
2-nitrobenzaldehyde + NADPH
2-nitrobenzyl alcohol + NADP+
2-nitrobenzaldehyde + NADPH
2-nitrobenzylalcohol + NADP+
-
-
-
-
?
2-octanone + NADPH + H+
? + NADP+
2-oxo-2-phenylacetaldehyde + NADH + H+
? + NAD+
-
-
-
?
2-oxo-2-phenylacetaldehyde + NADPH + H+
(S)-1-phenylethane-1,2-diol + NADP+
11% conversion, more than 99% S-enantiomeric excess
-
-
?
2-oxo-2-phenylacetaldehyde + NADPH + H+
? + NADP+
-
-
-
?
2-oxo-2-phenylacetic acid + NADPH + H+
? + NADP+
-
-
-
?
2-oxo-4-phenylbutanoate + NADPH + H+
(R)-2-hydroxy-4-phenylbutanoate + NADP+
2-oxobutyric acid + NADPH
2-hydroxybutyric acid + NADP+
-
low activity
-
-
?
2-pentanol + NADP+
2-pentanone + NADPH + H+
-
-
-
-
r
2-pentanone + NADPH
2-pentanol + NADP+
-
-
-
-
?
2-phthalimido-ethyl-3-oxobutanoate + NADPH + H+
ethyl (3R)-2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-3-hydroxybutanoate + NADP+
-
reduction of the beta-keto group to stereospecifically give the (R)-alcohol
-
-
?
2-propanol + NADP+
propanone + NADPH + H+
-
-
2-propanone i.e. acetone
-
r
3'-fluoroacetophenone + NADPH + H+
? + NADP+
3,4-hexandione + NADPH + H+
? + NADP+
low activity
-
-
?
3,5-bis(trifluoromethyl) acetophenone + NADPH + H+
(R)-[3,5-bis(trifluoromethyl)phenyl] ethanol + NADP+
-
-
-
-
?
3-benzoylpyridine + NADPH
(S)-alpha-phenyl-3-pyridylmethanol + NADP+
3-benzoylpyridine + NADPH
?
3-bromoacetophenone + NADPH + H+
1-(3-bromophenyl)ethanol + NADP+
-
61% conversion after 24 h
-
-
?
3-bromobenzaldehyde + NADPH + H+
3-bromobenzyl alcohol + NADP+
-
-
-
?
3-chlorobenzaldehyde + NADPH + H+
3-chlorobenzylalcohol + NADP+
-
-
-
-
?
3-fluorobenzaldehyde + NADPH + H+
3-fluorobenzyl alcohol + NADP+
-
-
-
?
3-glutathionyl-4-hydroxynonanal + NADP+
3-glutathionyl nonanoic-delta-lactone + NADPH + H+
-
oxidation of the hemiacetal form of 3-glutathionyl-4-hydroxynonanal, generating the 3-glutathionyl nonanoic-delta-lactone
-
?
3-glutathionyl-4-hydroxynonanal + NADP+
3-glutathionyl-1,4-dihydroxynonane + NADPH + H+
-
-
-
?
3-glutathionyl-4-hydroxynonanal + NADPH + H+
3-glutathionyl-1,4-dihydroxynonane + NADP+
3-glutathionyl-4-hydroxynonanal hemiacetal + NADPH + H+
3-glutathionyl-gamma-nonanolactone + NADP+
-
-
-
?
3-glutathionyl-hexanal + NADPH + H+
3-glutathionyl-hexan-1-ol + NADP+
-
-
-
?
3-glutathionyl-nonanal + NADPH + H+
3-glutathionyl-nonan-1-ol + NADP+
-
-
-
?
3-glutathionyl-propanal + NADPH + H+
3-glutathionyl-propan-1-ol + NADP+
-
-
-
?
3-hydroxybenzaldehyde + NADPH + H+
3-hydroxybenzyl alcohol + NADP+
3-nitroacetophenone + NADPH
1-(3-nitrophenyl)ethanol + NADP+
-
-
-
-
?
3-nitroacetophenone + NADPH
?
-
-
-
-
?
3-nitrobenzaldehyde + NADPH
3-nitrobenzyl alcohol + NADP+
-
-
-
-
?
3-nitrobenzaldehyde + NADPH
3-nitrobenzylalcohol + NADP+
-
-
-
-
?
3-nitrobenzaldehyde + NADPH + H+
3-nitrobenzyl alcohol + NADP+
7.0% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
3-oxo-3-(2,4-difluorophenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(2,4-difluorophenyl)propanenitrile + NADP+
-
-
92% yield, 98% enantiomeric excess
-
?
3-oxo-3-(3-methoxyphenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(3-methoxyphenyl)propanenitrile + NADP+
-
-
89% yield, 97% enantiomeric excess
-
?
3-oxo-3-(3-nitrophenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(3-nitrophenyl)propanenitrile + NADP+
-
-
87% yield, 99% enantiomeric excess
-
?
3-oxo-3-(4-bromophenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(4-bromophenyl)propanenitrile + NADP+
-
-
88% yield, 99% enantiomeric excess
-
?
3-oxo-3-(4-chlorophenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(4-chlorophenyl)propanenitrile + NADP+
-
-
90% yield, 99% enantiomeric excess
-
?
3-oxo-3-(4-cyanophenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(4-cyanophenyl)propanenitrile + NADP+
-
-
90% yield, 99% enantiomeric excess
-
?
3-oxo-3-(4-fluorophenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(4-fluorophenyl)propanenitrile + NADP+
-
-
90% yield, 99% enantiomeric excess
-
?
3-oxo-3-(4-methylphenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(4-methylphenyl)propanenitrile + NADP+
-
-
90% yield, 98% enantiomeric excess
-
?
3-oxo-3-(4-nitrophenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(4-nitrophenyl)propanenitrile + NADP+
-
-
86% yield, 99% enantiomeric excess
-
?
3-oxo-3-phenylpropanenitrile + NADPH
(R)-3-hydroxy-3-phenylpropanenitrile + NADP+
-
-
85% yield, 98% enantiomeric excess
-
?
3alpha-hydroxy-5beta-androstan-17-one + NADPH
?
-
-
-
-
?
4'-chloroacetophenone + NADPH + H+
(S)-1-(4-chlorophenyl)ethanol + NADP+
4'-fluoroacetophenone + NADPH + H+
? + NADP+
-
12.4% activity compared to ethyl 4-chloroacetoacetate
-
-
?
4-(6-methoxy-2-benzoxazolyl)acetophenone + NADPH
?
-
-
-
-
?
4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + NADPH + H+
4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol + NADP+
-
-
-
?
4-acetylpyridine + NADPH
?
-
-
-
-
?
4-acetylpyridine + NADPH
? + NADP+
-
-
-
-
?
4-benzoylpyridine + NADPH
?
4-benzoylpyridine + NADPH + H+
(S)-alpha-phenyl-4-pyridylmethanol + NADP+
4-benzoylpyridine + NADPH + H+
(S)-phenyl(pyridin-4-yl)methanol + NADP+
4-benzoylpyridine + NADPH + H+
? + NADP+
-
-
-
?
4-benzoylpyridine + NADPH + H+
phenyl-4-pyridylmethanol + NADP+
-
-
-
?
4-benzoylpyridine + NADPH + H+
S-(-)-phenylpyridin-4-yl-methynol + NADP+
-
stereoselective reduction
-
-
?
4-bromoacetophenone + NADPH + H+
(1S)-1-(4-bromophenyl)ethanol + (1R)-1-(4-bromophenyl)ethanol + NADP+
-
-
wild-type, (R)-configuration of product with 42% enantiomeric excess, mutant Q245H, (S)-configuration with 92%, mutant Q245P, with 98%, mutant Q245L, with 97% enantiomeric excess, respectively
-
?
4-bromobenzaldehyde + NADPH + H+
(4-bromophenyl)methanol + NADP+
4-bromobenzaldehyde + NADPH + H+
4-bromobenzyl alcohol + NADP+
-
-
-
?
4-carboxybenzaldehyde + NADPH
4-carboxybenzyl alcohol + NADP+
-
-
-
-
?
4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
reduction of 4-chloro-3-oxobutanoate to ethyl (S)-4-chloro-3-hydroxybutanoate by transformants in an aqueous mono-phase system for 18 h, gives a molar yield of 94% and an optical purity of the (S)-isomer of more than 99% enantiomeric excess
-
-
?
4-chloroacetophenone + NADPH + H+
(1S)-1-(4-chlorophenyl)ethanol + (1R)-1-(4-chlorophenyl)ethanol + NADP+
-
-
wild-type, (R)-configuration of product with 14% enantiomeric excess, mutant Q245H, (S)-configuration with 90%, mutant Q245P, with 96%, mutant Q245L, with 96% enantiomeric excess, respectively
-
?
4-chlorobenzaldehyde + NADPH + H+
(4-chlorophenyl)methanol + NADP+
4-chlorobenzaldehyde + NADPH + H+
4-chlorobenzylalcohol + NADP+
-
-
-
-
?
4-cyanobenzaldehyde + NADPH + H+
4-cyanobenzyl alcohol + NADP+
-
-
-
?
4-fluorobenzaldehyde + NADPH + H+
(4-fluorophenyl)methanol + NADP+
-
99% conversion
-
-
?
4-hexanoylpyridine + NADPH
1-(pyridin-4-yloxy)hexan-1-ol + NADP+
-
-
-
-
?
4-hexanoylpyridine + NADPH + H+
1-(pyridin-4-yloxy)hexan-1-ol + NADP+
4-hydroxy-2-hexenal + NADPH + H+
?
-
-
-
?
4-hydroxybenzaldehyde + NADPH + H+
4-hydroxybenzyl alcohol + NADP+
4-methoxyacetophenone + NADPH
(1S)-1-(4-methoxyphenyl)ethanol + (1R)-1-(4-methoxyphenyl)ethanol + NADP+
-
-
wild-type, (R)-configuration of product with 57% enantiomeric excess, mutant Q245H, (S)-configuration with 79%, mutant Q245P, with 98%, mutant Q245L, with 96% enantiomeric excess, respectively
-
?
4-methoxybenzaldehyde + NADPH + H+
4-methoxybenzyl alcohol + NADP+
4-methylacetophenone + NADPH + H+
(1S)-1-(4-methylphenyl)ethanol + (1R)-1-(4-methylphenyl)ethanol + NADP+
-
-
wild-type, (R)-configuration of product with 59% enantiomeric excess, mutant Q245H, (S)-configuration with 95%, mutant Q245P, with 96%, mutant Q245L, with 95% enantiomeric excess, respectively
-
?
4-methylbenzaldehyde + NADPH + H+
4-methylbenzyl alcohol + NADP+
-
-
-
?
4-methylnitrosamino-1-(3-pyridyl)-1-butanone + NADPH + H+
4-methylnitrosamino-1-(3-pyridyl)-1-butanol + NADP+
-
i.e. NNK, genotoxic compound from tobacco smoke, isozyme 11beta-HSD1, carbonyl reductase activity, EC 1.1.1.184
-
-
r
4-nitroacetophenone + NADPH
1-(4-nitrophenyl)ethanol + NADP+
-
native and recombinant enzymes, low activity
-
-
?
4-nitroacetophenone + NADPH
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
4-nitrobenzaldehyde + NADPH
4-nitrobenzylalcohol + NADP+
4-nitrobenzaldehyde + NADPH + H+
4-nitrobenzyl alcohol + NADP+
4-nitrobenzaldehyde + NADPH + H+
4-nitrobenzylalcohol + NADP+
4-oxo-2-nonenal + NADPH + H+
? + NADP+
-
9% of the activity with 9,10-phenanthrenequinone
-
-
?
4-oxonon-2-enal + NADPH + H+
1-hydroxynon-2-en-4-one + NADP+
4-oxonon-2-enal + NADPH + H+
4-hydroxynon-2-enal + NADP+
4-oxonon-2-enal + NADPH + H+
4-oxononanal + 4-hydroxynon-2-enal + 1-hydroxynon-2-en-4-one + NADP+
-
molecular modeling of substrate binding in the active site
product identification, 4-hydroxynon-2-enal is the major product
-
?
4-oxonon-2-enal + NADPH + H+
4-oxononanal + NADP+
4-pregnen-3,20-dione + NADPH
?
-
isozymes CHCR1-3
-
-
ir
4-tert-butylacetophenone + NADPH + H+
(1S)-1-(4-tert-butylphenyl)ethanol + (1R)-1-(4-tert-butylphenyl)ethanol + NADP+
-
-
wild-type, (R)-configuration of product with 31% enantiomeric excess, mutant Q245H, (S)-configuration with 96%, mutant Q245P, with 99%, mutant Q245L, with 99% enantiomeric excess, respectively
-
?
5-bromoisatin + NADPH
?
Candida macedoniensis
-
-
-
-
?
5alpha-androstan-17beta-ol-3-one + NADPH
?
5alpha-androstane-17beta-ol-3-one + NADPH
? + NADP+
5alpha-androstane-3,17-dione + NADPH
?
5alpha-androstane-3,17-dione + NADPH
? + NADP+
5alpha-androstane-3alpha,17beta-diol + NADPH
?
-
isozymes CHCR1-3
-
-
r
5alpha-dihydrotestosterone + NADPH
?
-
only enzyme form CR1
-
-
?
5beta-androstan-17beta-ol-3-one + NADPH
?
5beta-androstane-3,17-dione + NADPH
?
5beta-dihydrotestosterone + NADPH
?
-
only enzyme form CR1
-
-
?
5beta-pregnan-3alpha-ol-20-one + NADPH
? + NADP+
5beta-pregnan-3beta-ol-20-one + NADPH
?
-
isozymes CHCR1-3
-
-
r
6-(4-acetyl-5-fluoropyridin-3-yl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide + NADPH + H+
6-[5-fluoro-4-[(1R)-1-hydroxyethyl]pyridin-3-yl]-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide + NADP+
selective substrate of human carbonyl reductase 1
-
-
?
9,10-phenanthrenequinone + NADPH
?
9,10-phenanthrenequinone + NADPH
? + NADP+
9,10-phenanthrenequinone + NADPH + H+
? + NADP+
9,10-phenanthroline + NADPH + H+
?
-
stereoselective reduction
-
-
?
9,10-phenantrenequinone + NADPH + H+
?
-
-
-
?
9-cis-retinal + NADPH
9-cis-retinol + NADP+
-
recombinant enzyme
-
-
?
9-cis-retinal + NADPH + H+
9-cis-retinol + NADP+
-
-
-
-
?
acenaphthenequinone + NADPH
? + NADP+
-
-
-
-
r
acetaldehyde + NADPH + H+
ethanol + NADP+
-
-
-
-
?
acetohexamide + NADPH
?
-
-
-
-
?
acetohexamide + NADPH + H+
?
-
-
-
-
?
acetone + NADPH
2-propanol + NADP+
-
-
-
-
?
acetone + NADPH
propan-2-ol + NADP+
acetone + NADPH + H+
2-propanol + NADP+
-
-
-
?
acetone + NADPH + H+
propan-2-ol + NADP+
acetophenone + NADH + H+
(R)-1-phenylethan-1-ol + NAD+
-
-
-
?
acetophenone + NADPH + H+
(1S)-1-phenylethanol + (1R)-1-phenylethanol + NADP+
-
-
wild-type, (R)-configuration of product with 42% enantiomeric excess, mutant Q245H, (S)-configuration with 78%, mutant Q245P, with 64%, mutant Q245L, with 82% enantiomeric excess, respectively
-
?
acetophenone + NADPH + H+
(1S)-1-phenylethanol + NADP+
-
-
-
-
?
acetophenone + NADPH + H+
(R)-1-phenylethan-1-ol + NADP+
88.5% conversion, 35% R-enantiomeric excess
-
-
?
adrenochrome + NADPH + H+
?
-
stereoselective reduction
-
-
?
all-trans retinal + NADPH + H+
all-trans retinol + NADP+
-
-
-
-
?
all-trans-retinal + NADPH + H+
all-trans-retinol + NADP+
all-trans-retinol + NADP+
all-trans-retinal + NADPH
-
-
-
-
r
alpha-acetoxyacetophenone + NADPH + H+
?
-
-
-
-
?
alpha-bromoacetophenone + NADPH + H+
? + NADP+
-
-
-
?
alpha-chloroacetophenone + NADPH + H+
? + NADP+
-
40.6% activity compared to ethyl 4-chloroacetoacetate
-
-
?
alpha-naphthoquinone + NADPH
?
Candida macedoniensis
-
-
-
-
?
alpha-tocopherolquinone + NADPH
?
-
-
-
-
?
befunolol + NADPH
?
-
-
-
-
?
benzalacetone + NADPH
?
-
-
-
-
?
benzaldehyde + NADH + H+
benzyl alcohol + NAD+
benzaldehyde + NADPH
benzyl alcohol + NADP+
benzaldehyde + NADPH
benzylalcohol + NADP+
-
-
-
-
?
benzaldehyde + NADPH + H+
benzyl alcohol + NADP+
benzaldehyde + NADPH + H+
benzylalcohol + NADP+
-
-
-
-
?
benzil + NADPH
? + NADP+
-
recombinant enzyme
-
-
?
benzoylformic acid ethyl ester + NADPH
? + NADP+
-
-
-
-
r
benzoylpyridine + NADPH + H+
?
-
-
-
-
r
bupropion + NADPH + H+
erythrohydrobupropion + NADP+
-
-
in liver cytosol, antidepressant bupropion is reduced to erythrohydrobupropion and threohydrobupropion
-
?
bupropion + NADPH + H+
threohydrobupropion + NADP+
-
-
in liver cytosol, antidepressant bupropion is reduced to erythrohydrobupropion and threohydrobupropion
-
?
butyrophenone + NADPH
1-phenylbutan-1-ol + NADP+
-
-
-
-
?
butyrophenone + NADPH + H+
(1S)-1-phenylbutan-1-ol + NADP+
-
-
over 90% chiral purity of the alcohol product
-
?
camphorquinone + NADPH
? + NADP+
-
-
-
-
?
camphorquinone + NADPH + H+
?
-
-
-
-
?
camphorquinone + NADPH + H+
camphorquinol + NADP+
-
-
-
-
?
carnitine + NADPH + H+
?
-
-
-
-
?
chloromethyl 3-oxobutyrate + NADPH + H+
chloromethyl (S)-3-hydroxybutyrate + NADP+
-
-
97% purity of the S-enantiomer
-
?
cinnamaldehyde + NADH + H+
? + NAD+
-
-
-
?
cinnamaldehyde + NADPH + H+
? + NADP+
-
-
-
?
cortisol + NADPH + H+
20beta-dihydrocortisol + NADP+
crotonaldehyde + NADPH
2-buten-1-ol + NADP+
-
-
-
-
?
cycloheptanone + NADPH + H+
cycloheptanol + NADP+
-
-
-
-
?
cyclohex-2-en-1-ol + NADPH
cyclohex-2-en-1-one + NADP+
-
-
-
-
?
cyclohexanol + NADP+
cyclohexanone + NADPH + H+
cyclohexanone + NADPH
cyclohexanol + NADP+
cyclopentanol + NADP+
cyclopentanone + NADPH + H+
-
-
-
-
r
cyclopentanone + NADPH
cyclopentanol + NADP+
-
low activity
-
-
?
D-xylose + NADPH
? + NADP+
Cylindrocarpon sclerotigenum
-
very low activity
-
-
ir
daunorubicin + NADPH
daunorubicinol + NADP+
daunorubicin + NADPH + H+
daunorubicinol + NADP+
decanal + NADPH
decanol + NADP+
-
-
-
-
?
DELTA4-androstan-17beta-ol-3-one + NADPH
?
-
isozymes CHCR1-3
-
-
r
diacetyl + NADPH
?
-
-
-
-
?
diacetyl + NADPH
? + NADP+
diacetyl + NADPH + H+
(3S)-acetoin + NADP+
diacetyl + NADPH + H+
acetoin + NADP+
dihydrokawain + NADPH + H+
?
-
-
-
-
?
dihydroxyacetone + NADPH + H+
? + NADP+
-
-
-
?
dihydroxyacetone + NADPH + H+
glycerol + NADP+
doxorubicin + NADPH
doxorubicinol + NADP+
-
-
-
?
doxorubicin + NADPH + H+
doxorubicinol + NADP+
duroquinone + NADPH
?
-
-
-
-
?
estrone + NADPH + H+
estradiol + NADP+
-
-
-
?
ethyl 2-chloro-3-oxobutanoate + NADPH + H+
(S)-ethyl 2-chloro-3-hydroxybutanoate + NADP+
135.7% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
ethyl 2-chloro-3-oxobutanoate + NADPH + H+
? + NADP+
-
-
-
?
ethyl 2-chloro-3-oxobutanoate + NADPH + H+
ethyl 2-chloro-3-hydroxybutanoate + NADP+
-
-
-
-
?
ethyl 2-chloro-3-oxobutanoate + NADPH + H+
ethyl-2-chloro-3-hydroxybutanoate + NADP+
-
-
-
-
?
ethyl 2-ketopantothenate + NADPH
?
Candida macedoniensis
-
-
-
-
?
ethyl 2-methyl-3-oxobutanoate + NADPH + H+
ethyl 3-hydroxy-2-methylbutanoate + NADP+
-
-
-
?
ethyl 2-methylacetoacetate + NADPH + H+
? + NADP+
-
-
-
?
ethyl 2-oxo-3-phenylpropanoate + NADPH + H+
ethyl 2-hydroxy-3-phenylpropanoate + NADP+
128% of the activity with ethyl 2-methyl-3-oxobutanoate
-
-
?
ethyl 2-oxo-3-phenylpyruvate + NADPH + H+
ethyl 2-hydroxy-3-phenylpyruvate + NADP+
ethyl 2-oxo-4-phenylbutanoate + NADPH + H+
? + NADP+
-
-
-
?
ethyl 2-oxo-4-phenylbutanoate + NADPH + H+
ethyl (2S)-2-hydroxy-4-phenylbutanoate + NADP+
ethyl 2-oxo-4-phenylbutanoate + NADPH + H+
ethyl (R)-2-hydroxy-4-phenylbutanoate + NADP+
ethyl 2-oxo-4-phenylbutyrate + NADPH + H+
? + NADP+
-
-
-
?
ethyl 2-oxo-4-phenylbutyrate + NADPH + H+
ethyl 2-hydroxy-4-phenylbutyrate + NADP+
ethyl 2-oxobutanoate + NADPH + H+
ethyl 2-hydroxybutanoate + NADP+
-
16% activity compared to ethyl 4-chloro-3-oxobutanoate
-
-
r
ethyl 2-oxophenylacetate + NADPH + H+
? + NADP+
-
-
-
?
ethyl 2-oxopropanoate + NADPH + H+
ethyl 2-hydroxypropanoate + NADP+
41% of the activity with ethyl 2-methyl-3-oxobutanoate
-
-
?
ethyl 3,3-dimethyl-2-oxobutanoate + NADPH + H+
ethyl 3,3-dimethyl-2-hydroxybutanoate + NADP+
-
reduction of the sterically bulky ketone to the corresponding alcohol with excellent optical purity
-
-
?
ethyl 3,3-dimethyl-2-oxobutyrate + NADPH + H+
(S)-ethyl 3,3-dimethyl-2-hydroxybutyrate + NADP+
-
stereoselective reaction
over 90% chiral purity of the alcohol product
-
?
ethyl 3-methyl-2-oxobutanoate + NADPH + H+
? + NADP+
-
-
-
?
ethyl 3-methyl-2-oxobutanoate + NADPH + H+
ethyl (2R)-2-hydroxy-3-methylbutanoate + NADP+
-
95% conversion, 98.3% enantiomeric excess
-
?
ethyl 3-oxo-3-phenylpropionate + NADPH + H+
? + NADP+
-
-
-
?
ethyl 3-oxobutanoate + NADPH
ethyl 3-hydroxybutanoate + NADP+
-
-
-
-
?
ethyl 3-oxobutanoate + NADPH + H+
? + NADP+
-
-
-
?
ethyl 3-oxobutanoate + NADPH + H+
ethyl (3S)-3-hydroxybutanoate + NADP+
ethyl 3-oxobutanoate + NADPH + H+
ethyl 3-hydroxybutanoate + NADP+
25.2% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
ethyl 3-oxobutyrate + NADPH + H+
ethyl (R,S)-3-hydroxybutyrate + NADP+
-
-
61% S-enantiomer
-
?
ethyl 3-oxopentanoate + NADPH + H+
ethyl (R,S)-3-hydroxypentanoate + NADP+
-
-
61% S-enantiomer
-
?
ethyl 3-oxopentanoate + NADPH + H+
ethyl (S)-3-hydroxypentanoate + NADP+
-
-
99% conversion, 99% enantiomeric excess
-
?
ethyl 4,4,4-trifluoro-3-oxobutanoate + NADPH + H+
? + NADP+
-
-
-
?
ethyl 4,4,4-trifluoro-3-oxobutanoate + NADPH + H+
ethyl (3R)-4,4,4-trifluoro-3-hydroxybutanoate + NADP+
74% of the activity with 2-chloroacetophenone
100% conversion, 99% enantiomeric excess
-
?
ethyl 4,4,4-trifluoro-3-oxobutanoate + NADPH + H+
ethyl (3S)-4,4,4-trifluoro-3-hydroxybutyrate + NADP+
-
-
90% purity of the S-enantiomer
-
?
ethyl 4,4-dimethyl-3-oxopentanoate + NADPH + H+
ethyl 4,4-dimethyl-3-hydroxypentanoate + NADP+
-
reduction of the sterically bulky ketone to the corresponding alcohol with excellent optical purity
-
-
?
ethyl 4-chloro-3-oxobutanoate + NAD(P)H + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NAD(P)+
ethyl 4-chloro-3-oxobutanoate + NADPH
ethyl-4-chloro-3-hydroxybutanoate + NADP+
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
(S)-ethyl 4-chloro-3-hydroxybutanoate + NADP+
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (3R)-4-chloro-3-hydroxybutanoate + NADP+
8776% of the activity with 2-chloroacetophenone
100% conversion, 62% enantiomeric excess
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (3S)-4-chloro-3-hydroxybutanoate + NADP+
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (R)-4-chloro-3-hydroxybutanoate + NADP+
-
99% conversion, 92% enantiomeric excess
99% conversion, 92% enantiomeric excess
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl 4-chloro-3-hydroxybutanoate + NADP+
ethyl 4-chloroacetoacetate + NADPH + H+
? + NADP+
ethyl 4-chloroacetoacetate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
ethyl 4-chloroacetoacetate + NADPH + H+
ethyl S-4-chloro-3-hydroxybutyrate + NADP+
ethyl 5-oxohexanoate + NADPH
ethyl-5-hydroxyhexanoate + NADP+
-
-
-
-
?
ethyl acetoacetate + NADPH
? + NADP+
-
-
-
?
ethyl acetoacetate + NADPH + H+
ethyl S-3-hydroxybutyrate + NADP+
-
23.7% activity compared to ethyl 4-chloroacetoacetate
-
-
?
ethyl benzoylformate + NADPH
? + NADP+
-
-
-
?
ethyl benzoylformate + NADPH + H+
? + NADP+
ethyl pyruvate + NADPH + H+
?
-
-
-
-
?
ethyl pyruvate + NADPH + H+
ethyl (2S)-2-hydroxypropanoate + NADP+
7821% of the activity with 2-chloroacetophenone
100% conversion, 99% enantiomeric excess
-
?
ethyl pyruvate + NADPH + H+
ethyl 2-hydroxypropanoic acid + NADP+
ethyl pyruvate + NADPH + H+
ethyl lactate + NADP+
-
-
-
?
ethyl-2-oxo-2-phenylacetate + NADH + H+
(RS)-ethyl-2-hydroxy-2-phenylacetate + NAD+
ethyl-2-oxo-2-phenylacetate + NADH + H+
? + NAD+
-
-
-
?
ethyl-2-oxo-2-phenylacetate + NADPH + H+
(RS)-ethyl-2-hydroxy-2-phenylacetate + NADP+
100% conversion, 70% S-enantiomeric excess
-
-
?
ethyl-2-oxo-2-phenylacetate + NADPH + H+
? + NADP+
-
-
-
?
ethyl-2-oxo-4-phenylbutanoate + NADH + H+
(RS)-ethyl-2-hydroxy-4-phenylbutanoate + NAD+
84% conversion
-
-
?
ethyl-2-oxo-4-phenylbutanoate + NADPH + H+
(R)-ethyl-2-hydroxy-4-phenylbutanoate + NADP+
92% conversion, more than 99% R-enantiomeric excess
-
-
?
ethyl-2-oxo-4-phenylbutanoate + NADPH + H+
(RS)-ethyl-2-hydroxy-4-phenylbutanoate + NADP+
98% conversion, 70% S-enantiomeric excess
-
-
?
ethyl-4,4,4-trifloro-3-oxo-butanoate + NADH + H+
? + NAD+
-
-
-
?
ethyl-4,4,4-trifloro-3-oxo-butanoate + NADPH + H+
(R)-ethyl-4,4,4-trifluoro-3-hydroxybutanoate + NADP+
15% conversion, 69% R-enantiomeric excess
-
-
?
ethyl-4,4,4-trifloro-3-oxo-butanoate + NADPH + H+
? + NADP+
-
-
-
?
ethylpyruvate + NADPH
? + NADP+
Cylindrocarpon sclerotigenum
-
low activity
-
-
ir
fluoxetine + NADPH + H+
?
-
-
-
-
?
furfural + NADPH + H+
furfuryl alcohol + NADP+
-
-
-
?
glutaraldehyde + NADPH
? + NADP+
-
low activity
-
-
?
glutathione-4-oxonon-2-enal + NADPH + H+
glutathione-4-hydroxynon-2-enal + NADP+
glutathione-4-oxononanal + NADPH + H+
glutathione-4-hydroxynonanal + NADP+
-
conjugate, molecular modeling of substrate binding in the active site
-
-
?
glutathionyl-nonanal + NADPH + H+
?
-
-
-
?
heptanal + NADPH + H+
heptan-1-ol + NADP+
heptanophenone + NADPH
1-phenylheptan-1-ol + NADP+
hexanal + NADPH + H+
hexan-1-ol + NADP+
hexanophenone + NADPH
1-phenylhexan-1-ol + NADP+
hexaphenone + NADPH
1-phenylhexan-1-ol + NADP+
-
native and recombinant enzymes
-
-
?
hydrindantin + NADPH
?
-
-
-
-
?
hydroxyacetone + NADPH
? + NADP+
Cylindrocarpon sclerotigenum
-
low activity
-
-
ir
hydroxyacetone + NADPH + H+
glycerol + NADP+
-
-
-
?
hydroxyacetophenone + NAD+
(R)-1-phenyl-1,2-ethanediol + NADH + H+
-
-
-
?
indole 3-acetaldehyde + NADPH
indole-3-ol + NADP+
-
-
-
-
?
isatin + NADPH + H+
3-hydroxy-2-oxoindole + NADP+
isatin + NADPH + H+
? + NADP+
-
-
-
?
isoamyl pyruvate + NADPH + H+
isoamyl lactate + NADP+
-
-
-
?
isopropyl 2-ketopantothenate + NADPH
?
Candida macedoniensis
-
-
-
-
?
isopropyl 3-oxobutyrate + NADPH + H+
isopropyl (S)-3-hydroxybutyrate + NADP+
-
-
99% purity of the S-enantiomer
-
?
isovaleraldehyde + NADPH + H+
isoamyl alcohol + NADP+
ketopantoyl lactone + NADPH
(R)-pantolactone + NADP+
-
-
-
-
?
ketopantoyl lactone + NADPH
?
loxoprofen + NADPH
?
-
-
-
-
?
menadione + NADPH
? + NADP+
menadione + NADPH + H+
? + NADP+
methyl 2-chloro-3-oxobutanoate + NADPH + H+
(S)-methyl 2-chloro-3-hydroxybutanoate + NADP+
methyl 2-ketopantothenate + NADPH
?
Candida macedoniensis
-
-
-
-
?
methyl 2-oxo-3-phenylpropanoate + NADPH + H+
methyl 2-hydroxy-3-phenylpropanoate + NADP+
-
86.3% of the activity with ethyl 2-oxo-4-phenylbutanoate
-
-
?
methyl 2-oxo-4-phenylbutanoate + NADPH + H+
methyl (R)-2-hydroxy-4-phenylbutanoate + NADP+
-
88.5% of the activity with ethyl 2-oxo-4-phenylbutanoate
-
-
?
methyl 2-oxopropanoate + NADPH + H+
methyl (2S)-2-hydroxypropanoate + NADP+
-
67% conversion, 99.9% enantiomeric excess
-
?
methyl 4-chloro-3-oxobutanoate + NADPH + H+
(S)-methyl 4-chloro-3-hydroxybutanoate + NADP+
25.4% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
methyl 4-chloro-3-oxobutanoate + NADPH + H+
methyl 4-chloro-3-hydroxybutanoate + NADP+
-
9% activity compared to ethyl 4-chloro-3-oxobutanoate
-
-
r
methyl 4-chloroacetoacetate + NADPH
methyl (S)-4-chloro-3-hydroxybutanoate + NADP+
-
highly enantioselective reduction
-
-
ir
methyl benzoylformate + NADPH + H+
? + NADP+
-
79.4% of the activity with ethyl 2-oxo-4-phenylbutanoate
-
-
?
methyl glyoxal + NADPH
? + NADP+
-
-
-
-
?
methyl glyoxal + NADPH + H+
? + NADP+
methyl pyruvate + NADPH
methyl lactate + NADP+
-
-
-
-
?
methyl-1,4-benzoquinone + NADPH
?
-
-
-
-
?
methyl-2-oxobutanoate + NADPH + H+
? + NADP+
-
-
-
?
methyl-2-oxopropanoate + NADPH + H+
? + NADP+
-
-
-
?
methylglyoxal + NADPH
?
-
-
-
-
?
methylglyoxal + NADPH
? + NADP+
-
very low activity
-
-
ir
methylglyoxal + NADPH + H+
? + NADP+
-
-
-
?
mitroxantrone + NADPH + H+
?
N,N-dimethyl-3-keto-2-thienyl-propanamine + NADPH
(S)-N,N-dimethyl-3-keto-2-thienyl-propanamine + NADP+
-
-
key intermediate in synthesis of (S)-duloxetine
-
?
N,N-dimethyl-3-keto-3-(2-thienyl)-1-keto propanamine + NADPH + H+
(S)-3-(dimethylamino)-1-(2-thienyl)-1-propanol + NADP+
-
mutant enzyme A89N/F154Y with yield of 91.2% and S-enantiomeric excess of 99.9%
-
-
?
n-butylaldehyde + NADPH
n-butanol + NADP+
-
-
-
-
?
n-butyrophenone + NADPH
1-phenylbutan-1-ol + NADP+
n-hexylaldehyde + NADPH
n-hexanol + NADP+
-
low activity
-
-
?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
naphthazarin + NADPH + H+
?
nonanophenone + NADPH
1-phenylnonan-1-ol + NADP+
-
recombinant enzyme
-
-
?
octanal + NADPH + H+
1-octanol + NADP+
-
-
-
-
?
octanal + NADPH + H+
octan-1-ol + NADP+
-
-
-
?
octyl 4-chloro-3-oxobutanoate + NADPH
octyl 4-chloro-3-hydroxybutanoate + NADP+
-
-
-
-
?
octyl 4-chloro-3-oxobutanoate + NADPH
octyl-4-chloro-3-hydroxybutanoate + NADP+
Candida macedoniensis
-
-
-
-
?
oracin + NADPH + H+
11-dihydrooracin + NADP+
-
-
-
?
oracin + NADPH + H+
dihydrooracin + NADP+
oxalacetic acid + NADPH
? + NADP+
-
-
-
-
?
p-anisaldehyde + NADPH + H+
p-anisalcohol + NADP+
-
-
-
?
p-toluquinone + NADPH
?
Candida macedoniensis
-
-
-
-
?
p-toluquinone + NADPH
? + NADP+
-
-
-
?
p-toluquinone + NADPH + H+
? + NADP+
-
-
-
?
pentanal + NADPH + H+
pentan-1-ol + NADP+
phenyl 3-oxobutyrate + NADPH + H+
phenyl (S,R)-3-hydroxybutyrate + NADP+
-
-
56% S-enantiomer
-
?
phenyl cyclopropyl ketone + NADPH + H+
?
-
-
-
-
?
phenylglyoxal + 2 NADPH + 2 H+
(R)-1-phenyl-1,2-ethanediol + 2 NADP+
-
-
99% yield and 99% enantiomeric excess, by coupling with D-glucose dehydrogenase for the regeneration of cofactor NADPH
-
?
phenylglyoxal + NADPH + H+
? + NADP+
-
-
-
?
polyketid + NADPH
?
-
enzyme acts on the nascent polyketid chain from polyketid synthase reaction and reduces the carbonyl group at C-9
-
-
?
propanal + NADPH + H+
propan-1-ol + NADP+
propionaldehyde + NADPH
propanol + NADP+
-
low activity
-
-
?
propiophenone + NADPH
1-phenylpropan-1-ol + NADP+
prostaglandin A1 + NADPH
?
-
isozymes CHCR1 and 2, no activity with isozyme CHCR3
-
-
r
prostaglandin A1-GSH + NADPH
?
prostaglandin A2 + NADPH
?
-
isozymes CHCR1 and 2, no activity with isozyme CHCR3
-
-
r
prostaglandin B2 + NADPH
?
prostaglandin D2 + NADPH
?
-
isozymes CHCR1 and 2, no activity with isozyme CHCR3
-
-
r
prostaglandin E1 + NADPH + H+
?
-
-
-
-
r
prostaglandin E2 + NADPH
?
prostaglandin E2 + NADPH
prostaglandin F2alpha + NADP+
prostaglandin E2 + NADPH + H+
prostaglandin F2alpha + NADP+
prostaglandin F2alpha + NADPH
?
-
isozymes CHCR1 and 2, no activity with isozyme CHCR3
-
-
r
pyrenophorin + NADPH + H+
?
-
-
-
-
?
pyridin-4-carboxyaldehyde + NADPH
pyridin-4-ylmethanol + NADP+
-
artificial substrate
-
-
?
pyridine-3-aldehyde + NADPH
?
pyridine-3-aldehyde + NADPH
pyridin-3-ylbutanol + NADP+
-
native and recombinant enzymes, low activity
-
-
?
pyridine-4-aldehyde + NADPH
?
pyridine-4-aldehyde + NADPH + H+
pyridin-4-ylmethanol + NADP+
pyridine-4-carboxaldehyde + NADPH
?
-
-
-
-
?
S-1-phenyl-1-butanol + NADPH
? + NADP+
-
-
-
-
?
S-nitrosoglutathione + NADPH + H+
? + NADP+
t-butyl 6-cyano-(5R)-hydroxy-3-oxohexanoate + NADPH + H+
t-butyl 6-cyano-(3R,5R)-dihydroxyhexanoate + NADP+
tert-butyl 3-oxobutyrate + NADPH + H+
tert-butyl (S)-3-hydroxybutyrate + NADP+
-
-
99% purity of the S-enantiomer
-
?
testosterone + NADPH + H+
?
trans-4-phenyl-3-buten-2-one + NADPH
trans-4-phenyl-3-buten-2-ol + NADP+
-
also reacts with NADH, produces only R-enatiomer
-
-
?
ubiquinone-1 + NADPH
?
-
-
-
-
?
valeraldehyde + NADPH + H+
pentan-1-ol + NADP+
-
-
-
?
valerophenone + NADPH
1-phenylpentan-1-ol + NADP+
xestospongin A + NADPH + H+
?
-
-
-
-
?
additional information
?
-
(R)-2-butanol + NADP+
2-butanone + NADPH + H+
-
-
-
-
?
(R)-2-butanol + NADP+
2-butanone + NADPH + H+
-
-
-
-
?
(S)-2-butanol + NADP+
2-butanone + NADPH + H+
-
-
-
-
?
(S)-2-butanol + NADP+
2-butanone + NADPH + H+
-
-
-
-
?
1,4-naphthoquinone + NADPH + H+
? + NADP+
-
-
-
?
1,4-naphthoquinone + NADPH + H+
? + NADP+
-
native and recombinant enzymes, low activity
-
-
?
1-(3-methyl-1,4-dioxidoquinoxalin-2-yl)ethanone + NADPH + H+
1-(3-methyl-1,4-dioxidoquinoxalin-2-yl)ethanol + NADP+
i.e. mequindox, synthetic quinoxaline derivative, inhibitory to several Gram-positive and Gram-negative bactria
-
-
?
1-(3-methyl-1,4-dioxidoquinoxalin-2-yl)ethanone + NADPH + H+
1-(3-methyl-1,4-dioxidoquinoxalin-2-yl)ethanol + NADP+
i.e. mequindox, synthetic quinoxaline derivative, inhibitory to several Gram-positive and Gram-negative bacteria
-
-
?
1-(3-methyl-4-oxidoquinoxalin-2-yl)ethanone + NADPH + H+
1-(3-methyl-4-oxidoquinoxalin-2-yl)ethanol + NADP+
-
-
-
?
1-(3-methyl-4-oxidoquinoxalin-2-yl)ethanone + NADPH + H+
1-(3-methyl-4-oxidoquinoxalin-2-yl)ethanol + NADP+
-
-
-
?
1-(3-nitrosophenyl)ethan-1-one + NADPH + H+
1-(3-nitrosophenyl)ethan-1-ol + NADP+
-
86% conversion after 24 h, 99% R-enantiomeric excess
-
-
?
1-(3-nitrosophenyl)ethan-1-one + NADPH + H+
1-(3-nitrosophenyl)ethan-1-ol + NADP+
-
86% conversion after 24 h, 99% R-enantiomeric excess
-
-
?
1-(4-chlorophenyl)ethan-1-one + NADPH + H+
1-(4-chlorophenyl)ethan-1-ol + NADP+
-
41% conversion after 24 h, 99% S-enantiomeric excess
-
-
?
1-(4-chlorophenyl)ethan-1-one + NADPH + H+
1-(4-chlorophenyl)ethan-1-ol + NADP+
-
41% conversion after 24 h, 99% S-enantiomeric excess
-
-
?
1-(4-chlorophenyl)ethanone + NADPH + H+
(S)-1-(4-chlorophenyl)ethanol + NADP+
-
-
86% conversion, 99% enantiomeric excess
-
?
1-(4-chlorophenyl)ethanone + NADPH + H+
(S)-1-(4-chlorophenyl)ethanol + NADP+
-
-
86% conversion, 99% enantiomeric excess
-
?
1-(4-nitrosophenyl)ethan-1-one + NADPH + H+
1-(4-nitrosophenyl)ethan-1-ol + NADP+
-
30% conversion after 24 h, 73% S-enantiomeric excess
-
-
?
1-(4-nitrosophenyl)ethan-1-one + NADPH + H+
1-(4-nitrosophenyl)ethan-1-ol + NADP+
-
30% conversion after 24 h, 73% S-enantiomeric excess
-
-
?
1-acetonaphthone + NADPH
? + NADP+
-
-
-
-
?
1-acetonaphthone + NADPH
? + NADP+
-
-
-
-
?
1-acetonaphtone + NADPH + H+
? + NADP+
-
-
-
-
?
1-acetonaphtone + NADPH + H+
? + NADP+
-
-
-
-
?
1-phenyl-1,2-propandione + NADPH + H+
(R)-1-phenyl-2-hydroxy-1-propanone + NADP+
-
-
-
?
1-phenyl-1,2-propandione + NADPH + H+
(R)-1-phenyl-2-hydroxy-1-propanone + NADP+
-
-
-
?
1-phenyl-1,2-propandione + NADPH + H+
(S)-1-phenyl-2-hydroxy-1-propanone + NADP+
-
-
-
?
1-phenyl-1,2-propandione + NADPH + H+
(S)-1-phenyl-2-hydroxy-1-propanone + NADP+
-
-
-
?
1-phenylethan-1-one + NADPH + H+
1-phenylethan-1-ol + NADP+
-
75% conversion after 24 h, 99% S-enantiomeric excess
-
-
?
1-phenylethan-1-one + NADPH + H+
1-phenylethan-1-ol + NADP+
-
75% conversion after 24 h, 99% S-enantiomeric excess
-
-
?
1-phenylethanone + NADPH + H+
(S)-1-phenylethanol + NADP+
-
-
60% conversion, 99% enantiomeric excess
-
?
1-phenylethanone + NADPH + H+
(S)-1-phenylethanol + NADP+
-
-
60% conversion, 99% enantiomeric excess
-
?
1-phenylisatin + NADPH
? + NADP+
-
-
-
-
r
1-phenylisatin + NADPH
? + NADP+
-
-
-
?
1-phenylisatin + NADPH
? + NADP+
-
high activity, recombinant enzyme
-
-
?
13,14-dihydro-15-ketoprostaglandin F2alpha + NADPH
13,14-dihydroprostaglandin F2alpha + NADP+
-
-
-
?
13,14-dihydro-15-ketoprostaglandin F2alpha + NADPH
13,14-dihydroprostaglandin F2alpha + NADP+
-
-
-
?
16-ketoestrone + NADPH
? + NADP+
-
-
-
-
r
16-ketoestrone + NADPH
? + NADP+
-
recombinant enzyme
-
-
r
2'-fluoroacetophenone + NADPH + H+
? + NADP+
-
20.2% activity compared to ethyl 4-chloroacetoacetate
-
-
?
2'-fluoroacetophenone + NADPH + H+
? + NADP+
-
20.2% activity compared to ethyl 4-chloroacetoacetate
-
-
?
2,2,2-trifluoro-1-phenylethan-1-one + NADPH + H+
2,2,2-trifluoro-1-phenylethan-1-ol + NADP+
-
99.6% conversion after 24 h, 91.5% R-enantiomeric excess
-
-
?
2,2,2-trifluoro-1-phenylethan-1-one + NADPH + H+
2,2,2-trifluoro-1-phenylethan-1-ol + NADP+
-
99.6% conversion after 24 h, 91.5% R-enantiomeric excess
-
-
?
2,2,2-trifluoroacetophenone + NADPH + H+
(1S)-2,2,2-trifluoro-1-phenylethanol + NADP+
-
126.2% activity compared to ethyl 4-chloroacetoacetate
-
-
?
2,2,2-trifluoroacetophenone + NADPH + H+
(1S)-2,2,2-trifluoro-1-phenylethanol + NADP+
-
126.2% activity compared to ethyl 4-chloroacetoacetate
-
-
?
2,2,2-trifluoroacetophenone + NADPH + H+
(1S)-2,2,2-trifluoro-1-phenylethanol + NADP+
the preferred substrate is asymmetrically reduced in a coupled NADPH-regeneration system with an enantioselectivity of 99.8% and a conversion of 98%
-
-
r
2,2,2-trifluoroacetophenone + NADPH + H+
(1S)-2,2,2-trifluoro-1-phenylethanol + NADP+
best substrate, 462% of the activity with ethyl 2-methyl-3-oxobutanoate
-
-
?
2,2,2-trifluoroacetophenone + NADPH + H+
(1S)-2,2,2-trifluoro-1-phenylethanol + NADP+
the preferred substrate is asymmetrically reduced in a coupled NADPH-regeneration system with an enantioselectivity of 99.8% and a conversion of 98%
-
-
r
2,2,2-trifluoroacetophenone + NADPH + H+
(1S)-2,2,2-trifluoro-1-phenylethanol + NADP+
the preferred substrate is asymmetrically reduced in a coupled NADPH-regeneration system with an enantioselectivity of 99.8% and a conversion of 98%
-
-
r
2,2,2-trifluoroacetophenone + NADPH + H+
(R)-2,2,2-trifluoro-1-phenylethanol + NADP+
140% of the activity with 2-chloroacetophenone
100% conversion, 99% enantiomeric excess
-
?
2,2,2-trifluoroacetophenone + NADPH + H+
(R)-2,2,2-trifluoro-1-phenylethanol + NADP+
140% of the activity with 2-chloroacetophenone
100% conversion, 99% enantiomeric excess
-
?
2,3-butanedione + NADPH
? + NADP+
Cylindrocarpon sclerotigenum
-
-
-
-
ir
2,3-butanedione + NADPH
? + NADP+
-
-
-
?
2,3-butanedione + NADPH
? + NADP+
-
low activity
-
-
ir
2,3-butanedione + NADPH + H+
? + NADP+
-
-
-
?
2,3-butanedione + NADPH + H+
? + NADP+
-
-
-
?
2,3-butanedione + NADPH + H+
? + NADP+
35.2% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
2,3-heptandione + NADPH + H+
? + NADP+
-
-
-
?
2,3-heptandione + NADPH + H+
? + NADP+
-
-
-
?
2,3-hexandione + NADPH + H+
? + NADP+
-
-
-
?
2,3-hexandione + NADPH + H+
? + NADP+
-
-
-
?
2,3-hexanedione + NADPH + H+
? + NADP+
-
-
-
?
2,3-hexanedione + NADPH + H+
? + NADP+
-
-
-
?
2,3-hexanedione + NADPH + H+
? + NADP+
-
-
-
?
2,3-hexanedione + NADPH + H+
? + NADP+
17.3% of the activity with dihydroxyacetone
-
-
?
2,3-pentanedione + NADPH + H+
(R)-2-hydroxy-pentane-3-one + NADP+
-
-
-
?
2,3-pentanedione + NADPH + H+
(R)-2-hydroxy-pentane-3-one + NADP+
-
-
-
?
2,3-pentanedione + NADPH + H+
(S)-2-hydroxy-pentane-3-one + NADP+
-
-
-
?
2,3-pentanedione + NADPH + H+
(S)-2-hydroxy-pentane-3-one + NADP+
-
-
-
?
2,3-pentanedione + NADPH + H+
? + NADP+
-
-
-
-
r
2,3-pentanedione + NADPH + H+
? + NADP+
Cylindrocarpon sclerotigenum
-
low activity
-
-
ir
2,3-pentanedione + NADPH + H+
? + NADP+
-
-
-
-
ir
2,3-pentanedione + NADPH + H+
? + NADP+
58.6% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
2,3-pentanedione + NADPH + H+
? + NADP+
-
-
-
-
?
2-butanone + NADPH
2-butanol + NADP+
-
low activity
-
-
?
2-butanone + NADPH
2-butanol + NADP+
-
-
-
-
?
2-chloroacetophenone + NADPH + H+
(R)-2-chloro-1-phenylethanol + NADP+
-
74.5% conversion, 99% enantiomeric excess
-
?
2-chloroacetophenone + NADPH + H+
(R)-2-chloro-1-phenylethanol + NADP+
-
74.5% conversion, 99% enantiomeric excess
-
?
2-chloroacetophenone + NADPH + H+
(RS)-2-chloro-1-phenylethan-1-ol + NADP+
100% conversion
-
-
?
2-chloroacetophenone + NADPH + H+
(RS)-2-chloro-1-phenylethan-1-ol + NADP+
100% conversion
-
-
?
2-chlorobenzaldehyde + NADPH + H+
2-chlorobenzyl alcohol + NADP+
Candida macedoniensis
-
-
-
-
?
2-chlorobenzaldehyde + NADPH + H+
2-chlorobenzyl alcohol + NADP+
-
-
-
?
2-chlorobenzaldehyde + NADPH + H+
2-chlorobenzyl alcohol + NADP+
-
-
-
?
2-hydroxyacetophenone + NADH + H+
(S)-1-phenyl-1,2-ethanediol + NAD+
-
-
-
?
2-hydroxyacetophenone + NADH + H+
(S)-1-phenyl-1,2-ethanediol + NAD+
-
-
-
?
2-hydroxyacetophenone + NADH + H+
(S)-1-phenyl-1,2-ethanediol + NAD+
-
-
-
-
?
2-hydroxyacetophenone + NADH + H+
(S)-1-phenyl-1,2-ethanediol + NAD+
-
-
-
-
?
2-hydroxyacetophenone + NADPH + H+
(R)-1-phenyl-1,2-ethanediol + NADP+
-
-
-
?
2-hydroxyacetophenone + NADPH + H+
(R)-1-phenyl-1,2-ethanediol + NADP+
-
product of mutant enzyme S67D/H68D, 95.4% purity
-
?
2-hydroxyacetophenone + NADPH + H+
(RS)-1-phenyl-1,2-ethanediol + NADP+
100% conversion, more than 99% S-enantiomeric excess
-
-
?
2-hydroxyacetophenone + NADPH + H+
(RS)-1-phenyl-1,2-ethanediol + NADP+
100% conversion, more than 99% S-enantiomeric excess
-
-
?
2-hydroxyacetophenone + NADPH + H+
(S)-1-phenyl-1,2-ethanediol + NADP+
-
-
-
?
2-hydroxyacetophenone + NADPH + H+
(S)-1-phenyl-1,2-ethanediol + NADP+
-
-
-
-
?
2-hydroxyacetophenone + NADPH + H+
(S)-1-phenyl-1,2-ethanediol + NADP+
-
product of wild-type enzyme, 96.2% purity
-
?
2-nitrobenzaldehyde + NADPH
2-nitrobenzyl alcohol + NADP+
Candida macedoniensis
-
-
-
-
?
2-nitrobenzaldehyde + NADPH
2-nitrobenzyl alcohol + NADP+
-
-
-
-
?
2-nitrobenzaldehyde + NADPH
2-nitrobenzyl alcohol + NADP+
-
-
-
-
?
2-octanone + NADPH + H+
? + NADP+
-
64.6% activity compared to ethyl 4-chloroacetoacetate
-
-
?
2-octanone + NADPH + H+
? + NADP+
-
64.6% activity compared to ethyl 4-chloroacetoacetate
-
-
?
2-oxo-4-phenylbutanoate + NADPH + H+
(R)-2-hydroxy-4-phenylbutanoate + NADP+
-
77.1% of the activity with ethyl 2-oxo-4-phenylbutanoate
-
-
?
2-oxo-4-phenylbutanoate + NADPH + H+
(R)-2-hydroxy-4-phenylbutanoate + NADP+
-
77.1% of the activity with ethyl 2-oxo-4-phenylbutanoate
-
-
?
3'-fluoroacetophenone + NADPH + H+
? + NADP+
-
18.8% activity compared to ethyl 4-chloroacetoacetate
-
-
?
3'-fluoroacetophenone + NADPH + H+
? + NADP+
-
18.8% activity compared to ethyl 4-chloroacetoacetate
-
-
?
3-benzoylpyridine + NADPH
(S)-alpha-phenyl-3-pyridylmethanol + NADP+
-
recombinant enzyme
-
-
?
3-benzoylpyridine + NADPH
(S)-alpha-phenyl-3-pyridylmethanol + NADP+
-
highly stereoselective reaction, native and recombinant enzymes
-
-
?
3-benzoylpyridine + NADPH
?
-
-
-
-
?
3-benzoylpyridine + NADPH
?
-
-
-
-
?
3-glutathionyl-4-hydroxynonanal + NADPH + H+
3-glutathionyl-1,4-dihydroxynonane + NADP+
-
-
-
-
?
3-glutathionyl-4-hydroxynonanal + NADPH + H+
3-glutathionyl-1,4-dihydroxynonane + NADP+
-
-
-
?
3-glutathionyl-4-hydroxynonanal + NADPH + H+
3-glutathionyl-1,4-dihydroxynonane + NADP+
-
-
-
-
?
3-hydroxybenzaldehyde + NADPH + H+
3-hydroxybenzyl alcohol + NADP+
-
-
-
?
3-hydroxybenzaldehyde + NADPH + H+
3-hydroxybenzyl alcohol + NADP+
7.1% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
4'-chloroacetophenone + NADPH + H+
(S)-1-(4-chlorophenyl)ethanol + NADP+
64% of the activity with 2-chloroacetophenone
49.6% conversion, 99% enantiomeric excess
-
?
4'-chloroacetophenone + NADPH + H+
(S)-1-(4-chlorophenyl)ethanol + NADP+
64% of the activity with 2-chloroacetophenone
49.6% conversion, 99% enantiomeric excess
-
?
4-benzoylpyridine + NADPH
?
-
-
-
-
?
4-benzoylpyridine + NADPH
?
-
-
-
-
?
4-benzoylpyridine + NADPH
?
-
-
-
-
?
4-benzoylpyridine + NADPH
?
-
-
-
-
ir
4-benzoylpyridine + NADPH
?
-
-
-
-
?
4-benzoylpyridine + NADPH
?
-
-
-
-
?
4-benzoylpyridine + NADPH + H+
(S)-alpha-phenyl-4-pyridylmethanol + NADP+
-
-
-
-
?
4-benzoylpyridine + NADPH + H+
(S)-alpha-phenyl-4-pyridylmethanol + NADP+
-
-
-
-
?
4-benzoylpyridine + NADPH + H+
(S)-alpha-phenyl-4-pyridylmethanol + NADP+
-
isozymes CHCR1-3
-
-
ir
4-benzoylpyridine + NADPH + H+
(S)-alpha-phenyl-4-pyridylmethanol + NADP+
-
-
-
-
?
4-benzoylpyridine + NADPH + H+
(S)-alpha-phenyl-4-pyridylmethanol + NADP+
-
-
-
?
4-benzoylpyridine + NADPH + H+
(S)-alpha-phenyl-4-pyridylmethanol + NADP+
-
-
-
?
4-benzoylpyridine + NADPH + H+
(S)-alpha-phenyl-4-pyridylmethanol + NADP+
-
-
-
-
?
4-benzoylpyridine + NADPH + H+
(S)-alpha-phenyl-4-pyridylmethanol + NADP+
-
recombinant enzyme
-
-
?
4-benzoylpyridine + NADPH + H+
(S)-alpha-phenyl-4-pyridylmethanol + NADP+
-
highly stereoselective reaction, native and recombinant enzymes
-
-
?
4-benzoylpyridine + NADPH + H+
(S)-phenyl(pyridin-4-yl)methanol + NADP+
-
-
-
?
4-benzoylpyridine + NADPH + H+
(S)-phenyl(pyridin-4-yl)methanol + NADP+
-
-
-
?
4-benzoylpyridine + NADPH + H+
(S)-phenyl(pyridin-4-yl)methanol + NADP+
-
-
-
-
?
4-bromobenzaldehyde + NADPH + H+
(4-bromophenyl)methanol + NADP+
-
99% conversion
-
-
?
4-bromobenzaldehyde + NADPH + H+
(4-bromophenyl)methanol + NADP+
-
99% conversion
-
-
?
4-chlorobenzaldehyde + NADPH + H+
(4-chlorophenyl)methanol + NADP+
-
99% conversion
-
-
?
4-chlorobenzaldehyde + NADPH + H+
(4-chlorophenyl)methanol + NADP+
-
99% conversion
-
-
?
4-hexanoylpyridine + NADPH + H+
1-(pyridin-4-yloxy)hexan-1-ol + NADP+
-
recombinant enzyme
-
-
?
4-hexanoylpyridine + NADPH + H+
1-(pyridin-4-yloxy)hexan-1-ol + NADP+
-
native and recombinant enzymes
-
-
?
4-hydroxybenzaldehyde + NADPH + H+
4-hydroxybenzyl alcohol + NADP+
-
-
-
?
4-hydroxybenzaldehyde + NADPH + H+
4-hydroxybenzyl alcohol + NADP+
-
-
-
?
4-methoxybenzaldehyde + NADPH + H+
4-methoxybenzyl alcohol + NADP+
-
-
-
?
4-methoxybenzaldehyde + NADPH + H+
4-methoxybenzyl alcohol + NADP+
-
-
-
?
4-nitroacetophenone + NADPH
?
-
-
-
-
?
4-nitroacetophenone + NADPH
?
-
-
-
-
?
4-nitroacetophenone + NADPH
?
-
-
-
-
?
4-nitroacetophenone + NADPH
?
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
artificial substrate
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzylalcohol + NADP+
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzylalcohol + NADP+
-
native and recombinant enzymes
-
-
?
4-nitrobenzaldehyde + NADPH + H+
4-nitrobenzyl alcohol + NADP+
-
-
-
?
4-nitrobenzaldehyde + NADPH + H+
4-nitrobenzyl alcohol + NADP+
-
-
-
?
4-nitrobenzaldehyde + NADPH + H+
4-nitrobenzyl alcohol + NADP+
-
-
-
?
4-nitrobenzaldehyde + NADPH + H+
4-nitrobenzyl alcohol + NADP+
-
-
-
-
r
4-nitrobenzaldehyde + NADPH + H+
4-nitrobenzylalcohol + NADP+
-
-
-
?
4-nitrobenzaldehyde + NADPH + H+
4-nitrobenzylalcohol + NADP+
-
-
-
?
4-nitrobenzaldehyde + NADPH + H+
4-nitrobenzylalcohol + NADP+
-
-
-
?
4-oxonon-2-enal + NADPH + H+
1-hydroxynon-2-en-4-one + NADP+
-
-
-
-
?
4-oxonon-2-enal + NADPH + H+
1-hydroxynon-2-en-4-one + NADP+
-
metabolic inactivation of the lipid peroxidation product, pathway overview
-
-
?
4-oxonon-2-enal + NADPH + H+
4-hydroxynon-2-enal + NADP+
-
-
-
-
?
4-oxonon-2-enal + NADPH + H+
4-hydroxynon-2-enal + NADP+
-
metabolic inactivation of the lipid peroxidation product, pathway overview
-
-
?
4-oxonon-2-enal + NADPH + H+
4-oxononanal + NADP+
-
-
-
-
?
4-oxonon-2-enal + NADPH + H+
4-oxononanal + NADP+
-
metabolic inactivation of the lipid peroxidation product, pathway overview
-
-
?
5alpha-androstan-17beta-ol-3-one + NADPH
?
-
isozymes CHCR1-3
-
-
ir
5alpha-androstan-17beta-ol-3-one + NADPH
?
-
-
-
-
?
5alpha-androstan-17beta-ol-3-one + NADPH
?
-
-
-
-
?
5alpha-androstane-17beta-ol-3-one + NADPH
? + NADP+
-
-
-
-
?
5alpha-androstane-17beta-ol-3-one + NADPH
? + NADP+
-
-
-
-
?
5alpha-androstane-17beta-ol-3-one + NADPH
? + NADP+
-
-
-
?
5alpha-androstane-3,17-dione + NADPH
?
-
isozymes CHCR1-3
-
-
ir
5alpha-androstane-3,17-dione + NADPH
?
-
-
-
-
?
5alpha-androstane-3,17-dione + NADPH
?
-
only enzyme forms CR2, CR8
-
-
?
5alpha-androstane-3,17-dione + NADPH
?
-
-
-
-
?
5alpha-androstane-3,17-dione + NADPH
? + NADP+
-
-
-
-
?
5alpha-androstane-3,17-dione + NADPH
? + NADP+
-
-
-
-
?
5alpha-androstane-3,17-dione + NADPH
? + NADP+
-
-
-
?
5beta-androstan-17beta-ol-3-one + NADPH
?
-
only enzyme forms CR2, CR8
-
-
?
5beta-androstan-17beta-ol-3-one + NADPH
?
-
-
-
-
?
5beta-androstane-3,17-dione + NADPH
?
-
isozymes CHCR1-3
-
-
ir
5beta-androstane-3,17-dione + NADPH
?
-
only enzyme form CR1
-
-
?
5beta-androstane-3,17-dione + NADPH
?
-
-
-
-
?
5beta-pregnan-3alpha-ol-20-one + NADPH
? + NADP+
-
-
-
-
?
5beta-pregnan-3alpha-ol-20-one + NADPH
? + NADP+
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
? + NADP+
-
-
-
-
r
9,10-phenanthrenequinone + NADPH
? + NADP+
-
artificial substrate
-
-
?
9,10-phenanthrenequinone + NADPH
? + NADP+
-
-
-
?
9,10-phenanthrenequinone + NADPH
? + NADP+
-
best substrate, recombinant enzyme
-
-
r
9,10-phenanthrenequinone + NADPH + H+
? + NADP+
-
-
-
?
9,10-phenanthrenequinone + NADPH + H+
? + NADP+
-
-
-
?
9,10-phenanthrenequinone + NADPH + H+
? + NADP+
-
-
-
-
?
9,10-phenanthrenequinone + NADPH + H+
? + NADP+
-
-
-
?
9,10-phenanthrenequinone + NADPH + H+
? + NADP+
-
-
-
?
9,10-phenanthrenequinone + NADPH + H+
? + NADP+
-
-
-
?
acetone + NADPH
propan-2-ol + NADP+
-
-
-
-
?
acetone + NADPH
propan-2-ol + NADP+
-
-
-
-
r
acetone + NADPH
propan-2-ol + NADP+
-
-
-
-
?
acetone + NADPH + H+
propan-2-ol + NADP+
-
20.2% activity compared to ethyl 4-chloroacetoacetate
-
-
?
acetone + NADPH + H+
propan-2-ol + NADP+
-
20.2% activity compared to ethyl 4-chloroacetoacetate
-
-
?
all-trans-retinal + NADPH + H+
all-trans-retinol + NADP+
-
-
-
-
r
all-trans-retinal + NADPH + H+
all-trans-retinol + NADP+
-
recombinant enzyme
-
-
?
benzaldehyde + NADH + H+
benzyl alcohol + NAD+
-
-
-
?
benzaldehyde + NADH + H+
benzyl alcohol + NAD+
-
-
-
?
benzaldehyde + NADPH
benzyl alcohol + NADP+
-
-
-
-
?
benzaldehyde + NADPH
benzyl alcohol + NADP+
-
-
-
-
?
benzaldehyde + NADPH + H+
benzyl alcohol + NADP+
-
-
-
?
benzaldehyde + NADPH + H+
benzyl alcohol + NADP+
highest activity
-
-
?
benzaldehyde + NADPH + H+
benzyl alcohol + NADP+
highest activity
-
-
?
benzaldehyde + NADPH + H+
benzyl alcohol + NADP+
-
-
-
?
benzaldehyde + NADPH + H+
benzyl alcohol + NADP+
-
-
-
?
benzaldehyde + NADPH + H+
benzyl alcohol + NADP+
-
-
-
?
benzaldehyde + NADPH + H+
benzyl alcohol + NADP+
43% of the activity with ethyl 2-methyl-3-oxobutanoate
-
-
?
benzaldehyde + NADPH + H+
benzyl alcohol + NADP+
43% of the activity with ethyl 2-methyl-3-oxobutanoate
-
-
?
benzaldehyde + NADPH + H+
benzyl alcohol + NADP+
43% of the activity with ethyl 2-methyl-3-oxobutanoate
-
-
?
cortisol + NADPH + H+
20beta-dihydrocortisol + NADP+
-
-
-
-
?
cortisol + NADPH + H+
20beta-dihydrocortisol + NADP+
-
-
-
?
cortisol + NADPH + H+
20beta-dihydrocortisol + NADP+
-
-
-
?
cyclohexanol + NADP+
cyclohexanone + NADPH + H+
-
-
-
-
r
cyclohexanol + NADP+
cyclohexanone + NADPH + H+
-
-
-
-
r
cyclohexanone + NADPH
cyclohexanol + NADP+
-
-
-
-
?
cyclohexanone + NADPH
cyclohexanol + NADP+
-
-
-
-
?
daunorubicin + NADPH
?
-
isozymes CHCR1-3
-
-
ir
daunorubicin + NADPH
?
-
-
-
-
?
daunorubicin + NADPH
?
-
-
-
-
?
daunorubicin + NADPH
daunorubicinol + NADP+
-
-
-
-
?
daunorubicin + NADPH
daunorubicinol + NADP+
-
-
-
?
daunorubicin + NADPH + H+
daunorubicinol + NADP+
J9P7P2
-
-
-
?
daunorubicin + NADPH + H+
daunorubicinol + NADP+
-
-
-
?
daunorubicin + NADPH + H+
daunorubicinol + NADP+
-
-
-
-
?
daunorubicin + NADPH + H+
daunorubicinol + NADP+
-
-
-
?
daunorubicin + NADPH + H+
daunorubicinol + NADP+
reduction of the anthracycline C13 carbonyl results in a 13-hydroxy metabolite that elicits potent cardiotoxic effects while possessing significantly reduced anticancer properties
-
-
?
daunorubicin + NADPH + H+
daunorubicinol + NADP+
an anthracyclin, formation of a 13-hydroxy-anthracyclin
-
-
?
diacetyl + NADPH
? + NADP+
-
low activity
-
-
?
diacetyl + NADPH
? + NADP+
-
recombinant enzyme
-
-
?
diacetyl + NADPH + H+
(3S)-acetoin + NADP+
-
-
no synthesis of (2S,3S)-2,3-butanediol
-
?
diacetyl + NADPH + H+
(3S)-acetoin + NADP+
-
-
no synthesis of (2S,3S)-2,3-butanediol
-
?
diacetyl + NADPH + H+
acetoin + NADP+
-
-
-
-
?
diacetyl + NADPH + H+
acetoin + NADP+
-
-
-
-
?
diacetyl + NADPH + H+
acetoin + NADP+
-
-
-
-
r
dihydroxyacetone + NADPH + H+
glycerol + NADP+
-
-
-
?
dihydroxyacetone + NADPH + H+
glycerol + NADP+
-
-
-
?
doxorubicin + NADPH + H+
doxorubicinol + NADP+
-
-
-
?
doxorubicin + NADPH + H+
doxorubicinol + NADP+
-
-
-
-
?
doxorubicin + NADPH + H+
doxorubicinol + NADP+
-
-
-
?
doxorubicin + NADPH + H+
doxorubicinol + NADP+
reduction of the anthracycline C13 carbonyl results in a 13-hydroxy metabolite that elicits potent cardiotoxic effects while possessing significantly reduced anticancer properties
-
-
?
doxorubicin + NADPH + H+
doxorubicinol + NADP+
an anthracyclin, formation of a 13-hydroxy-anthracyclin
-
-
?
doxorubicin + NADPH + H+
doxorubicinol + NADP+
CBR1 is a predominant hepatic doxorubicin reductase
-
-
?
doxorubicin + NADPH + H+
doxorubicinol + NADP+
-
-
-
?
ethyl 2-oxo-3-phenylpyruvate + NADPH + H+
ethyl 2-hydroxy-3-phenylpyruvate + NADP+
-
97.7% of the activity with ethyl 2-oxo-4-phenylbutanoate
-
-
?
ethyl 2-oxo-3-phenylpyruvate + NADPH + H+
ethyl 2-hydroxy-3-phenylpyruvate + NADP+
-
97.7% of the activity with ethyl 2-oxo-4-phenylbutanoate
-
-
?
ethyl 2-oxo-4-phenylbutanoate + NADPH + H+
ethyl (2S)-2-hydroxy-4-phenylbutanoate + NADP+
576% of the activity with 2-chloroacetophenone
100% conversion, 85.7% enantiomeric excess
-
?
ethyl 2-oxo-4-phenylbutanoate + NADPH + H+
ethyl (2S)-2-hydroxy-4-phenylbutanoate + NADP+
576% of the activity with 2-chloroacetophenone
100% conversion, 85.7% enantiomeric excess
-
?
ethyl 2-oxo-4-phenylbutanoate + NADPH + H+
ethyl (R)-2-hydroxy-4-phenylbutanoate + NADP+
-
-
-
-
?
ethyl 2-oxo-4-phenylbutanoate + NADPH + H+
ethyl (R)-2-hydroxy-4-phenylbutanoate + NADP+
-
-
-
-
?
ethyl 2-oxo-4-phenylbutyrate + NADPH + H+
ethyl 2-hydroxy-4-phenylbutyrate + NADP+
-
-
-
?
ethyl 2-oxo-4-phenylbutyrate + NADPH + H+
ethyl 2-hydroxy-4-phenylbutyrate + NADP+
-
-
-
?
ethyl 3-oxobutanoate + NADPH + H+
ethyl (3S)-3-hydroxybutanoate + NADP+
145% of the activity with 2-chloroacetophenone
100% conversion, 99% enantiomeric excess
-
?
ethyl 3-oxobutanoate + NADPH + H+
ethyl (3S)-3-hydroxybutanoate + NADP+
145% of the activity with 2-chloroacetophenone
100% conversion, 99% enantiomeric excess
-
?
ethyl 4-chloro-3-oxobutanoate + NAD(P)H + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NAD(P)+
-
stereospecific reaction, formation of a hydrophobic channel induced by NADPH binding, structure overview
optically pure (S)-enantiomer
-
?
ethyl 4-chloro-3-oxobutanoate + NAD(P)H + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NAD(P)+
-
stereospecific reaction
optically pure (S)-enantiomer
-
?
ethyl 4-chloro-3-oxobutanoate + NAD(P)H + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NAD(P)+
-
stereospecific reaction
optically pure (S)-enantiomer
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH
ethyl-4-chloro-3-hydroxybutanoate + NADP+
Candida macedoniensis
-
-
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH
ethyl-4-chloro-3-hydroxybutanoate + NADP+
-
-
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH
ethyl-4-chloro-3-hydroxybutanoate + NADP+
-
only produces S-enantiomer
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
(S)-ethyl 4-chloro-3-hydroxybutanoate + NADP+
Cylindrocarpon sclerotigenum
-
highly stereoselective reduction
-
-
ir
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
(S)-ethyl 4-chloro-3-hydroxybutanoate + NADP+
-
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (3S)-4-chloro-3-hydroxybutanoate + NADP+
-
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (3S)-4-chloro-3-hydroxybutanoate + NADP+
enantioselectivity shows a strong dependence on temperature. Under optimal conditions of -3°C, (S)-4-chloro-3-hydroxybutanoate in 98% enantiomeric excess is produced
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
the enantioselectivity of NcCR for the reduction of ethyl 4-chloro-3-oxobutanoate shows a strong dependence on temperature. The enantiomeric excess is substantially increased by decreasing the temperature from 40°C (78.8%) to -3°C (98.0%)
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
the enantioselectivity of NcCR for the reduction of ethyl 4-chloro-3-oxobutanoate shows a strong dependence on temperature. The enantiomeric excess is substantially increased by decreasing the temperature from 40°C (78.8%) to -3°C (98.0%)
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
-
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
-
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl 4-chloro-3-hydroxybutanoate + NADP+
-
-
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl 4-chloro-3-hydroxybutanoate + NADP+
384% of the activity with ethyl 2-methyl-3-oxobutanoate
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl 4-chloro-3-hydroxybutanoate + NADP+
384% of the activity with ethyl 2-methyl-3-oxobutanoate
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl 4-chloro-3-hydroxybutanoate + NADP+
384% of the activity with ethyl 2-methyl-3-oxobutanoate
-
-
?
ethyl 4-chloroacetoacetate + NADPH + H+
? + NADP+
-
76.9% of the activity with ethyl 2-oxo-4-phenylbutanoate
-
-
?
ethyl 4-chloroacetoacetate + NADPH + H+
? + NADP+
-
76.9% of the activity with ethyl 2-oxo-4-phenylbutanoate
-
-
?
ethyl 4-chloroacetoacetate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
-
enantioselective reduction
-
-
ir
ethyl 4-chloroacetoacetate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
-
highly enantioselective reduction
-
-
ir
ethyl 4-chloroacetoacetate + NADPH + H+
ethyl S-4-chloro-3-hydroxybutyrate + NADP+
-
-
-
-
?
ethyl 4-chloroacetoacetate + NADPH + H+
ethyl S-4-chloro-3-hydroxybutyrate + NADP+
-
100% activity
-
-
?
ethyl benzoylformate + NADPH + H+
? + NADP+
-
90.8% of the activity with ethyl 2-oxo-4-phenylbutanoate
-
-
?
ethyl benzoylformate + NADPH + H+
? + NADP+
-
90.8% of the activity with ethyl 2-oxo-4-phenylbutanoate
-
-
?
ethyl pyruvate + NADPH + H+
ethyl 2-hydroxypropanoic acid + NADP+
-
-
-
-
?
ethyl pyruvate + NADPH + H+
ethyl 2-hydroxypropanoic acid + NADP+
-
24% activity compared to ethyl 4-chloro-3-oxobutanoate
-
-
r
ethyl-2-oxo-2-phenylacetate + NADH + H+
(RS)-ethyl-2-hydroxy-2-phenylacetate + NAD+
86% conversion
-
-
?
ethyl-2-oxo-2-phenylacetate + NADH + H+
(RS)-ethyl-2-hydroxy-2-phenylacetate + NAD+
86% conversion
-
-
?
glutathione-4-oxonon-2-enal + NADPH + H+
glutathione-4-hydroxynon-2-enal + NADP+
-
-
-
-
?
glutathione-4-oxonon-2-enal + NADPH + H+
glutathione-4-hydroxynon-2-enal + NADP+
-
metabolic inactivation of the lipid peroxidation product, pathway overview
-
-
?
heptanal + NADPH + H+
heptan-1-ol + NADP+
-
-
-
?
heptanal + NADPH + H+
heptan-1-ol + NADP+
-
-
-
?
heptanophenone + NADPH
1-phenylheptan-1-ol + NADP+
-
-
-
-
?
heptanophenone + NADPH
1-phenylheptan-1-ol + NADP+
-
-
-
-
?
heptanophenone + NADPH
1-phenylheptan-1-ol + NADP+
-
recombinant enzyme
-
-
?
hexanal + NADPH + H+
hexan-1-ol + NADP+
-
-
-
?
hexanal + NADPH + H+
hexan-1-ol + NADP+
-
-
-
?
hexanophenone + NADPH
1-phenylhexan-1-ol + NADP+
-
-
-
-
?
hexanophenone + NADPH
1-phenylhexan-1-ol + NADP+
-
-
-
-
?
hexanophenone + NADPH
1-phenylhexan-1-ol + NADP+
-
recombinant enzyme
-
-
?
isatin + NADPH
?
Candida macedoniensis
-
-
-
-
?
isatin + NADPH
?
-
isozymes CHCR1-3
-
-
ir
isatin + NADPH
? + NADP+
-
-
-
-
r
isatin + NADPH
? + NADP+
-
-
-
?
isatin + NADPH
? + NADP+
-
-
-
?
isatin + NADPH
? + NADP+
-
recombinant enzyme
-
-
r
isatin + NADPH + H+
3-hydroxy-2-oxoindole + NADP+
-
-
-
?
isatin + NADPH + H+
3-hydroxy-2-oxoindole + NADP+
-
-
-
?
isatin + NADPH + H+
3-hydroxy-2-oxoindole + NADP+
-
-
-
-
?
isatin + NADPH + H+
3-hydroxy-2-oxoindole + NADP+
-
-
-
?
isatin + NADPH + H+
3-hydroxy-2-oxoindole + NADP+
17.7% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
isovaleraldehyde + NADPH + H+
isoamyl alcohol + NADP+
-
-
-
?
isovaleraldehyde + NADPH + H+
isoamyl alcohol + NADP+
-
-
-
?
ketopantoyl lactone + NADPH
?
Candida macedoniensis
-
-
-
-
?
ketopantoyl lactone + NADPH
?
-
-
-
-
?
menadione + NADPH
?
Candida macedoniensis
-
-
-
-
?
menadione + NADPH
?
-
-
-
-
?
menadione + NADPH
?
-
-
-
-
?
menadione + NADPH
?
-
-
-
-
?
menadione + NADPH
?
-
best substrate
-
-
?
menadione + NADPH
?
-
-
-
-
?
menadione + NADPH
?
-
-
-
-
?
menadione + NADPH
? + NADP+
-
-
-
-
?
menadione + NADPH
? + NADP+
-
-
-
-
?
menadione + NADPH
? + NADP+
-
artificial substrate
-
-
?
menadione + NADPH
? + NADP+
-
-
-
-
?
menadione + NADPH
? + NADP+
-
-
-
?
menadione + NADPH
? + NADP+
-
-
-
?
menadione + NADPH
? + NADP+
-
-
-
?
menadione + NADPH
? + NADP+
-
recombinant enzyme
-
-
?
menadione + NADPH
? + NADP+
-
native and recombinant enzymes, low activity
-
-
?
menadione + NADPH + H+
?
-
-
-
-
?
menadione + NADPH + H+
?
-
-
-
?
menadione + NADPH + H+
?
reduction of the anthracycline C13 carbonyl results in a 13-hydroxy metabolite that elicits potent cardiotoxic effects while possessing significantly reduced anticancer properties
-
-
?
menadione + NADPH + H+
?
an anthracyclin, formation of a 13-hydroxy-anthracyclin
-
-
?
menadione + NADPH + H+
? + NADP+
J9P7P2
-
-
-
?
menadione + NADPH + H+
? + NADP+
-
-
-
?
menadione + NADPH + H+
? + NADP+
-
-
-
?
menadione + NADPH + H+
? + NADP+
-
-
-
?
menadione + NADPH + H+
? + NADP+
-
-
-
-
?
menadione + NADPH + H+
? + NADP+
-
-
-
?
menadione + NADPH + H+
? + NADP+
-
-
-
-
?
menadione + NADPH + H+
? + NADP+
-
48% of the activity with 9,10-phenanthrenequinone
-
-
?
menadione + NADPH + H+
? + NADP+
-
-
-
?
methyl 2-chloro-3-oxobutanoate + NADPH + H+
(S)-methyl 2-chloro-3-hydroxybutanoate + NADP+
25.1% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
methyl 2-chloro-3-oxobutanoate + NADPH + H+
(S)-methyl 2-chloro-3-hydroxybutanoate + NADP+
-
-
-
-
?
methyl glyoxal + NADPH + H+
? + NADP+
-
-
-
?
methyl glyoxal + NADPH + H+
? + NADP+
-
-
-
?
mitroxantrone + NADPH + H+
?
-
-
-
?
mitroxantrone + NADPH + H+
?
reduction of the anthracycline C13 carbonyl results in a 13-hydroxy metabolite that elicits potent cardiotoxic effects while possessing significantly reduced anticancer properties
-
-
?
mitroxantrone + NADPH + H+
?
an anthracyclin, formation of a 13-hydroxy-anthracyclin
-
-
?
n-butyrophenone + NADPH
1-phenylbutan-1-ol + NADP+
-
-
-
-
?
n-butyrophenone + NADPH
1-phenylbutan-1-ol + NADP+
-
recombinant enzyme
-
-
?
n-butyrophenone + NADPH
1-phenylbutan-1-ol + NADP+
-
native and recombinant enzymes, low activity
-
-
?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
naphthazarin + NADPH + H+
?
reduction of the anthracycline C13 carbonyl results in a 13-hydroxy metabolite that elicits potent cardiotoxic effects while possessing significantly reduced anticancer properties
-
-
?
naphthazarin + NADPH + H+
?
an anthracyclin, formation of a 13-hydroxy-anthracyclin
-
-
?
oracin + NADPH + H+
dihydrooracin + NADP+
-
a cytostatic drug, isozyme 11beta-HSD1, carbonyl reductase activity, EC 1.1.1.184, stereochemical ratio of 3:1 for R:S enantiomers of the pro-chiral carbonyl centre of oracin, inactivation of the anti-cancer drug
-
-
r
oracin + NADPH + H+
dihydrooracin + NADP+
-
a cytostatic drug, isozyme 11beta-HSD1, carbonyl reductase activity, EC 1.1.1.184, stereochemical ratio of 3:1 for R:S enantiomers of the pro-chiral carbonyl centre of oracin, inactivation reaction
-
-
r
pentanal + NADPH + H+
pentan-1-ol + NADP+
-
-
-
?
pentanal + NADPH + H+
pentan-1-ol + NADP+
-
-
-
?
phenylglyoxal + NADPH
?
-
-
-
-
?
phenylglyoxal + NADPH
?
-
-
-
-
?
phenylglyoxal + NADPH
?
-
-
-
-
?
propanal + NADPH + H+
propan-1-ol + NADP+
-
-
-
?
propanal + NADPH + H+
propan-1-ol + NADP+
-
-
-
?
propanal + NADPH + H+
propan-1-ol + NADP+
54% of the activity with ethyl 2-methyl-3-oxobutanoate
-
-
?
propiophenone + NADPH
1-phenylpropan-1-ol + NADP+
-
-
-
-
?
propiophenone + NADPH
1-phenylpropan-1-ol + NADP+
-
-
-
-
?
propiophenone + NADPH
1-phenylpropan-1-ol + NADP+
-
recombinant enzyme
-
-
?
propiophenone + NADPH
1-phenylpropan-1-ol + NADP+
-
native and recombinant enzymes, low activity
-
-
?
prostaglandin A1-GSH + NADPH
?
-
-
-
-
?
prostaglandin A1-GSH + NADPH
?
-
only enzyme forms T3, V1, V2
-
-
?
prostaglandin B2 + NADPH
?
-
isozymes CHCR1 and 2, no activity with isozyme CHCR3
-
-
r
prostaglandin B2 + NADPH
?
-
-
-
-
?
prostaglandin E2 + NADPH
?
-
isozymes CHCR1 and 2, no activity with isozyme CHCR3
-
-
r
prostaglandin E2 + NADPH
?
-
-
-
-
?
prostaglandin E2 + NADPH
?
-
only enzyme forms CR2, CR8
-
-
?
prostaglandin E2 + NADPH
prostaglandin F2alpha + NADP+
-
-
-
-
?
prostaglandin E2 + NADPH
prostaglandin F2alpha + NADP+
-
-
-
?
prostaglandin E2 + NADPH
prostaglandin F2alpha + NADP+
-
-
-
?
prostaglandin E2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
?
prostaglandin E2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
?
prostaglandin E2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
-
r
pyridine-3-aldehyde + NADPH
?
-
-
-
-
?
pyridine-3-aldehyde + NADPH
?
-
-
-
-
?
pyridine-3-aldehyde + NADPH
?
-
-
-
-
?
pyridine-3-aldehyde + NADPH
?
-
-
-
-
?
pyridine-3-aldehyde + NADPH
?
-
-
-
-
?
pyridine-4-aldehyde + NADPH
?
-
-
-
-
?
pyridine-4-aldehyde + NADPH
?
-
-
-
-
ir
pyridine-4-aldehyde + NADPH
?
-
-
-
-
?
pyridine-4-aldehyde + NADPH
?
-
-
-
-
?
pyridine-4-aldehyde + NADPH + H+
pyridin-4-ylmethanol + NADP+
-
-
-
-
?
pyridine-4-aldehyde + NADPH + H+
pyridin-4-ylmethanol + NADP+
-
recombinant enzyme
-
-
?
pyridine-4-aldehyde + NADPH + H+
pyridin-4-ylmethanol + NADP+
-
native and recombinant enzymes
-
-
?
S-nitrosoglutathione + NADPH + H+
? + NADP+
-
-
-
?
S-nitrosoglutathione + NADPH + H+
? + NADP+
no substrate for wild-type, but substrate for mutants D236A/K238P/D239K/S240A/I241T/R242K/T243S/V244P, P230W/D236A/K238P/D239K/S240A/I241T/R242K/T243S/V244P, and Q142M/C143S/P230W/D236A/K238P/D239K/S240A/I241T/R242K/T243S/V244P/H270S
-
-
?
t-butyl 6-cyano-(5R)-hydroxy-3-oxohexanoate + NADPH + H+
t-butyl 6-cyano-(3R,5R)-dihydroxyhexanoate + NADP+
-
high stereoselectivity, 94% conversion in 4 h
-
-
?
t-butyl 6-cyano-(5R)-hydroxy-3-oxohexanoate + NADPH + H+
t-butyl 6-cyano-(3R,5R)-dihydroxyhexanoate + NADP+
-
high stereoselectivity, 94% conversion in 4 h
-
-
?
testosterone + NADPH + H+
?
-
-
-
?
testosterone + NADPH + H+
?
-
-
-
-
?
valerophenone + NADPH
1-phenylpentan-1-ol + NADP+
-
-
-
-
?
valerophenone + NADPH
1-phenylpentan-1-ol + NADP+
-
-
-
-
?
valerophenone + NADPH
1-phenylpentan-1-ol + NADP+
-
recombinant enzyme
-
-
?
valerophenone + NADPH
1-phenylpentan-1-ol + NADP+
-
native and recombinant enzymes
-
-
?
additional information
?
-
Candida macedoniensis
-
very low activity with NADH
-
-
?
additional information
?
-
-
NADPH can only partially replace NADH as coenzyme
-
-
?
additional information
?
-
-
uses only S-enantiomers of methyl-3-hydroxybutanoate, 2-butanol, phenylethanol
-
-
?
additional information
?
-
no reaction with 2-chloroacetophenone plus NADH or 2-hydroxyacetophenone plus NADH
-
-
-
additional information
?
-
the reduction of aldehydes is cofactor (NADPH) specific unlike the alpha-ketoesters which show dual specificity i.e. both NADH and NADPH
-
-
-
additional information
?
-
the reduction of aldehydes is cofactor (NADPH) specific unlike the alpha-ketoesters which show dual specificity i.e. both NADH and NADPH
-
-
-
additional information
?
-
no reaction with 2-chloroacetophenone plus NADH or 2-hydroxyacetophenone plus NADH
-
-
-
additional information
?
-
-
no reaction with 2-chloroacetophenone plus NADH or 2-hydroxyacetophenone plus NADH
-
-
-
additional information
?
-
-
overview
-
-
?
additional information
?
-
-
overview
-
-
?
additional information
?
-
-
overview
-
-
?
additional information
?
-
-
overview
-
-
?
additional information
?
-
-
NADH also acts as cofactor
-
-
?
additional information
?
-
-
NADH also acts as cofactor
-
-
?
additional information
?
-
-
NADH also acts as cofactor
-
-
?
additional information
?
-
-
ordered bi bi mechanism
-
-
?
additional information
?
-
-
low reverse direction only detected with cyclohexanol
-
-
?
additional information
?
-
-
specificity of various enzyme forms
-
-
?
additional information
?
-
-
substrate specificities of the 3 isozymes, overview, no activity with 5alpha-androstan-3beta-ol-17-one
-
-
?
additional information
?
-
-
no activity with 5alpha-androstane-3alpha-ol-17-one
-
-
?
additional information
?
-
Cylindrocarpon sclerotigenum
-
enzyme shows highly restricted substrate specificity, overview
-
-
?
additional information
?
-
-
stereospecific enzyme, substrate binding mechanism, active site cleft
-
-
?
additional information
?
-
-
sniffer prevents age-dependent and oxidative stress-induced neurodegeneration in Drosophila melanogaster, formation of 4-hydroxyalkenals due to lipoprotein oxidation, and is shown to drive macrophage uptake and sub-intimal accumulation of oxidized lipids and lesion progression
-
-
?
additional information
?
-
-
NADH only acts as cofactor for enzyme form CR1
-
-
?
additional information
?
-
reduction of alpha-diketones is regio- and stereospecific producing the corresponding 2R-hydroxy-ketone
-
-
?
additional information
?
-
reduction of alpha-diketones is regio- and stereospecific producing the corresponding 2R-hydroxy-ketone
-
-
?
additional information
?
-
reduction of alpha-diketones is regio- and stereospecific producing the corresponding 2S-hydroxy-ketone
-
-
?
additional information
?
-
reduction of alpha-diketones is regio- and stereospecific producing the corresponding 2S-hydroxy-ketone
-
-
?
additional information
?
-
reduction of alpha-diketones is regio- and stereospecific producing the corresponding 2S-hydroxy-ketone
-
-
?
additional information
?
-
reduction of alpha-diketones is regio- and stereospecific producing the corresponding 2S-hydroxy-ketone
-
-
?
additional information
?
-
-
reduction of alpha-diketones is regio- and stereospecific producing the corresponding 2S-hydroxy-ketone
-
-
?
additional information
?
-
reduction of alpha-diketones is regio- and stereospecific producing the corresponding 2R-hydroxy-ketone
-
-
?
additional information
?
-
reduction of alpha-diketones is regio- and stereospecific producing the corresponding 2R-hydroxy-ketone
-
-
?
additional information
?
-
-
reduction of alpha-diketones is regio- and stereospecific producing the corresponding 2R-hydroxy-ketone
-
-
?
additional information
?
-
-
-
-
-
?
additional information
?
-
-
overview
-
-
?
additional information
?
-
-
overview
-
-
?
additional information
?
-
-
no activity with 1-hydroxynon-2-en-4-one and 4-hydroxynon-2-enal
-
-
?
additional information
?
-
-
the enzyme interconvertes 11-oxo-glucocorticoids to their 11-hydroxy metabolites, reaction of EC 1.1.1.146, but is also active as carbonyl reductase, EC 1.1.1.184, in detoxification of xenobiotic carbonyl compounds reducing them to alcohols that are easier to conjugate and eliminate
-
-
?
additional information
?
-
-
the enzyme is responsible for detoxifcation of reactive aldehydes, CR has a potential physiological role for neuroprotection in humans and represents a signifcant pathway for the detoxifcation of reactive aldehydes derived from lipid peroxidation, CR is essential for neuronal cell survival and to confer protection against oxidative stress-induced brain degeneration, overview
-
-
?
additional information
?
-
-
the enzyme metabolizes prostaglandins, steroids, quinines, and anthracycline antibiotics, enzyme expression is inversely associated with tumor progression and angiogenesis
-
-
?
additional information
?
-
-
the enzyme is active with steroids and prostaglandins
-
-
?
additional information
?
-
-
the enzyme shows pluripotent substrate specificity being active as 11beta-hydroxysteroid dehydrogenase, EC 1.1.1.146, and carbonyl reductase, EC 1.1.1.184
-
-
?
additional information
?
-
CBR1 3'-untranslated region polymorphism 1096G-A in DNA samples from whites, and livers with homozygous G/G genotypes show a trend toward higher CBR1 mRNA levels compared with samples with heterozygous G/A genotypes. CBR1 1096G-A genotype status is associated with CBR1 protein levels
-
-
?
additional information
?
-
-
CBR1 3'-untranslated region polymorphism 1096G-A in DNA samples from whites, and livers with homozygous G/G genotypes show a trend toward higher CBR1 mRNA levels compared with samples with heterozygous G/A genotypes. CBR1 1096G-A genotype status is associated with CBR1 protein levels
-
-
?
additional information
?
-
inactive towards menadione
-
-
?
additional information
?
-
inactive towards menadione
-
-
?
additional information
?
-
-
no activity with 5alpha-androstane-3alpha-ol-17-one
-
-
?
additional information
?
-
no doxorubicin or menadione reduction is catalyzed by CBR3
-
-
?
additional information
?
-
-
no doxorubicin or menadione reduction is catalyzed by CBR3
-
-
?
additional information
?
-
single nucleotide polymorphism V88I and P131S mutations exhibit a 20 to 40% decrease in catalytic efficiency (kcat/Km) compared with that for the wild-type enzyme
-
-
?
additional information
?
-
-
single nucleotide polymorphism V88I and P131S mutations exhibit a 20 to 40% decrease in catalytic efficiency (kcat/Km) compared with that for the wild-type enzyme
-
-
?
additional information
?
-
-
carbonyl reductase oxidizes the hydroxyl group of 3-glutathionyl-4-hydroxynonanal in its hemiacetal form, with the formation of the corresponding 3-glutathionyl nonanoic-delta-lactone. The enzyme is practically inactive toward trans-4-hydroxy-2-nonenal, buthionine sulfoximine, N-acetylcysteine
-
-
?
additional information
?
-
the presence of the glutathionyl moiety in the substrates appears as a necessary requirement for the susceptibility by hCBR1. The corresponding alkanals and alkenals, and the cysteinyl and gamma-glutamyl-cysteinylalkanals adducts are either ineffective or very poorly active as CBR1 substrates
-
-
?
additional information
?
-
-
the presence of the glutathionyl moiety in the substrates appears as a necessary requirement for the susceptibility by hCBR1. The corresponding alkanals and alkenals, and the cysteinyl and gamma-glutamyl-cysteinylalkanals adducts are either ineffective or very poorly active as CBR1 substrates
-
-
?
additional information
?
-
-
enzyme is a reductase no dehydrogenase, no activity with phenylglyoxal, 2,4-pentanedione, ethyl 3-oxobutanoate, or methyl 3-oxobutanoate, no activity with nitrobenzaldehydes, xylose, isatin, acetone, acetophenone, propionaldehyde, and pyridine 3-aldehyde, enzyme might be an alpha-subunit of the fatty acid synthase due to amino acid sequence identity, but does not show fatty acid synthase activity
-
-
?
additional information
?
-
-
asymmetric reduction, anti- and syndiastereoselective reactions, overview, identification of products
-
-
?
additional information
?
-
strong activities are observed toward linear aldehydes, such as 1-heptanal, valeraldehyde and 1-octanal, but no activity toward 5-hydroxymethylfurfural, propionaldehyde, D-alanine, L-alanine,D-lactate, L-lactate or pyruvate. Enzyme does not exhibit NADP+-dependent oxidative activity toward corresponding alcohol analogs, including 1-hexanol, 1-heptanol, isoamyl alcohol, isobutanol, 1-octanol and 2-propanol
-
-
?
additional information
?
-
strong activities are observed toward linear aldehydes, such as 1-heptanal, valeraldehyde and 1-octanal, but no activity toward 5-hydroxymethylfurfural, propionaldehyde, D-alanine, L-alanine,D-lactate, L-lactate or pyruvate. Enzyme does not exhibit NADP+-dependent oxidative activity toward corresponding alcohol analogs, including 1-hexanol, 1-heptanol, isoamyl alcohol, isobutanol, 1-octanol and 2-propanol
-
-
?
additional information
?
-
-
strong activities are observed toward linear aldehydes, such as 1-heptanal, valeraldehyde and 1-octanal, but no activity toward 5-hydroxymethylfurfural, propionaldehyde, D-alanine, L-alanine,D-lactate, L-lactate or pyruvate. Enzyme does not exhibit NADP+-dependent oxidative activity toward corresponding alcohol analogs, including 1-hexanol, 1-heptanol, isoamyl alcohol, isobutanol, 1-octanol and 2-propanol
-
-
?
additional information
?
-
strong activities are observed toward linear aldehydes, such as 1-heptanal, valeraldehyde and 1-octanal, but no activity toward HMF, propionaldehyde, D-alanine, L-alanine,D-lactate, L-lactate or pyruvate. Enzyme does not exhibit NADP+-dependent oxidative activity toward corresponding alcohol analogs, including 1-hexanol, 1-heptanol, isoamyl alcohol, isobutanol, 1-octanol and 2-propanol
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additional information
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strong activities are observed toward linear aldehydes, such as 1-heptanal, valeraldehyde and 1-octanal, but no activity toward HMF, propionaldehyde, D-alanine, L-alanine,D-lactate, L-lactate or pyruvate. Enzyme does not exhibit NADP+-dependent oxidative activity toward corresponding alcohol analogs, including 1-hexanol, 1-heptanol, isoamyl alcohol, isobutanol, 1-octanol and 2-propanol
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additional information
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strong activities are observed toward linear aldehydes, such as 1-heptanal, valeraldehyde and 1-octanal, but no activity toward HMF, propionaldehyde, D-alanine, L-alanine,D-lactate, L-lactate or pyruvate. Enzyme does not exhibit NADP+-dependent oxidative activity toward corresponding alcohol analogs, including 1-hexanol, 1-heptanol, isoamyl alcohol, isobutanol, 1-octanol and 2-propanol
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additional information
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strong activities are observed toward linear aldehydes, such as 1-heptanal, valeraldehyde and 1-octanal, but no activity toward 5-hydroxymethylfurfural, propionaldehyde, D-alanine, L-alanine,D-lactate, L-lactate or pyruvate. Enzyme does not exhibit NADP+-dependent oxidative activity toward corresponding alcohol analogs, including 1-hexanol, 1-heptanol, isoamyl alcohol, isobutanol, 1-octanol and 2-propanol
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additional information
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strong activities are observed toward linear aldehydes, such as 1-heptanal, valeraldehyde and 1-octanal, but no activity toward 5-hydroxymethylfurfural, propionaldehyde, D-alanine, L-alanine,D-lactate, L-lactate or pyruvate. Enzyme does not exhibit NADP+-dependent oxidative activity toward corresponding alcohol analogs, including 1-hexanol, 1-heptanol, isoamyl alcohol, isobutanol, 1-octanol and 2-propanol
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additional information
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strong activities are observed toward linear aldehydes, such as 1-heptanal, valeraldehyde and 1-octanal, but no activity toward HMF, propionaldehyde, D-alanine, L-alanine,D-lactate, L-lactate or pyruvate. Enzyme does not exhibit NADP+-dependent oxidative activity toward corresponding alcohol analogs, including 1-hexanol, 1-heptanol, isoamyl alcohol, isobutanol, 1-octanol and 2-propanol
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additional information
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strong activities are observed toward linear aldehydes, such as 1-heptanal, valeraldehyde and 1-octanal, but no activity toward HMF, propionaldehyde, D-alanine, L-alanine,D-lactate, L-lactate or pyruvate. Enzyme does not exhibit NADP+-dependent oxidative activity toward corresponding alcohol analogs, including 1-hexanol, 1-heptanol, isoamyl alcohol, isobutanol, 1-octanol and 2-propanol
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additional information
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enzyme is able to reduce both aldehydes and ketones
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additional information
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enzyme is able to reduce both aldehydes and ketones
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additional information
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the enzyme catalyses the oxidation of various secondary and cyclic alcohols to the corresponding ketones and the reverse reaction. No primary alcohols are oxidized. 1,3-Butandiol, glycerol, methanol, ethanol, 1,2-ethandiol, 1-propanol, 1-amino-2-propanol, 1-butanol, 1-pentanol, 1-hexanol and benzylalcohol are not oxidized nor are the respective aldehydes or ketones reduced
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additional information
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the enzyme catalyses the oxidation of various secondary and cyclic alcohols to the corresponding ketones and the reverse reaction. No primary alcohols are oxidized. 1,3-Butandiol, glycerol, methanol, ethanol, 1,2-ethandiol, 1-propanol, 1-amino-2-propanol, 1-butanol, 1-pentanol, 1-hexanol and benzylalcohol are not oxidized nor are the respective aldehydes or ketones reduced
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additional information
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overview
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additional information
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overview
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additional information
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NADH also acts as cofactor
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additional information
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the recombinant enzyme exhibits a restricted substrate spectrum towards various ketones, and the highest activity is observed with dihydroxyacetone, while hydroxyacetone is reduced with only 0.2% of the activity achieved with dihydroxyacetone, among aliphatic and aromatic ketones and aldehydes. The enzyme proves to be very selective in the reduction of different alpha- and beta-keto esters. Several compounds are converted to the corresponding hydroxy ester in high enantiomeric excess at high conversion rates. Diketones are also accepted by the enzyme. Highest activities are obtained with alpha,beta-diketones carrying the two ketogroups near the end of the aliphatic chain. No or poor activity with 2,5-hexandione, 2-cyclohexen-1-one, cyclohexanone, 2-methylcyclohexanone, 2-pentanone, 4-phenyl-2-butanone, cyclopropyl methyl ketone, trans-3-nonen-2-one, 2-butanone, 2-methyl-2-cyclopenten-1-one, and beta-ionone. The enantioselectivity of the enzyme reaction is highly increased at lower temperatures, overview
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additional information
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the recombinant enzyme exhibits a restricted substrate spectrum towards various ketones, and the highest activity is observed with dihydroxyacetone, while hydroxyacetone is reduced with only 0.2% of the activity achieved with dihydroxyacetone, among aliphatic and aromatic ketones and aldehydes. The enzyme proves to be very selective in the reduction of different alpha- and beta-keto esters. Several compounds are converted to the corresponding hydroxy ester in high enantiomeric excess at high conversion rates. Diketones are also accepted by the enzyme. Highest activities are obtained with alpha,beta-diketones carrying the two ketogroups near the end of the aliphatic chain. No or poor activity with 2,5-hexandione, 2-cyclohexen-1-one, cyclohexanone, 2-methylcyclohexanone, 2-pentanone, 4-phenyl-2-butanone, cyclopropyl methyl ketone, trans-3-nonen-2-one, 2-butanone, 2-methyl-2-cyclopenten-1-one, and beta-ionone. The enantioselectivity of the enzyme reaction is highly increased at lower temperatures, overview
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additional information
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the recombinant enzyme exhibits a restricted substrate spectrum towards various ketones, and the highest activity is observed with dihydroxyacetone, while hydroxyacetone is reduced with only 0.2% of the activity achieved with dihydroxyacetone, among aliphatic and aromatic ketones and aldehydes. The enzyme proves to be very selective in the reduction of different alpha- and beta-keto esters. Several compounds are converted to the corresponding hydroxy ester in high enantiomeric excess at high conversion rates. Diketones are also accepted by the enzyme. Highest activities are obtained with alpha,beta-diketones carrying the two ketogroups near the end of the aliphatic chain. No or poor activity with 2,5-hexandione, 2-cyclohexen-1-one, cyclohexanone, 2-methylcyclohexanone, 2-pentanone, 4-phenyl-2-butanone, cyclopropyl methyl ketone, trans-3-nonen-2-one, 2-butanone, 2-methyl-2-cyclopenten-1-one, and beta-ionone. The enantioselectivity of the enzyme reaction is highly increased at lower temperatures, overview
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additional information
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substrate specificity
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additional information
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no activity with NADH
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additional information
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overview
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additional information
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overview
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additional information
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no activity with NADH
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additional information
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specificity of various enzyme forms
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additional information
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no activity with 5alpha-androstane-3alpha-ol-17-one
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additional information
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no activity with 5beta-pregnan-3alpha-ol-20-one
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additional information
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enzyme is highly stereospecific, broad range substrate specificity
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additional information
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high enantioselectivity and broad substrate specificity, overview
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additional information
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no activity for methyl-3-oxobutanoate and simple ketones and aldehydes such as benzaldehyde and acrolein. No substrate: pyridine-4-aldehyde, ethyl 4,4,4-trifluoro-3-oxobutanoate, pyridine-3-aldehyde or p-nitrobenzaldehyde
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additional information
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broad substrate specificity, overview
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additional information
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the enzyme performs enantioselective reductions of sterically bulky aryl alkyl ketones, overview
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additional information
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reduces ethyl 4-chloro-3-oxobutanoate selectively to S-product
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additional information
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substrate specificity, detailed overview, the enzyme shows anti-Prelog enantioselectivity, the enzyme catalyzes the reduction of a series of ketones, alpha- and beta-ketoesters, synthesis of several chiral alcohol intermediates of pharmaceutical importance
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additional information
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overview
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additional information
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overview
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additional information
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substrate specificity, overview
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additional information
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NADH also acts as cofactor
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additional information
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catalyzes pro-S stereoselective hydrogen transfer from NADPH
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additional information
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substrate specificity, no activity with 3-nitroacetophenone and 4-acetylpyridine, catalytic activity of the recombinant enzyme is similar to the native enzyme
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additional information
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the enzyme plays a role in superoxide formation through redox cycling of 9,10-phenanthrenequinone and, to a lesser extent, of adrenochrome in pig heart
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additional information
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the enzyme catalyses the NADPH-linked reduction of a variety of carbonyl compounds to their secondary alcohols
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additional information
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the recombinant enzyme exhibits broad substrate specificity towards various keto esters, ketones and aldehydes, detailed overview
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additional information
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the recombinant enzyme exhibits broad substrate specificity towards various keto esters, ketones and aldehydes, detailed overview
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additional information
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gene contains the conserved catalytic tetrad D-Y-K-H (Asp53, Tyr58, Lys84, and His117) and putative cofactor binding sites at Asp53, Ser147, Asn148, Gln169, Glu249, and Asn254
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additional information
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gene contains the conserved catalytic tetrad D-Y-K-H (Asp53, Tyr58, Lys84, and His117) and putative cofactor binding sites at Asp53, Ser147, Asn148, Gln169, Glu249, and Asn254
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additional information
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the recombinant enzyme exhibits broad substrate specificity towards various keto esters, ketones and aldehydes, detailed overview
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?
additional information
?
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gene contains the conserved catalytic tetrad D-Y-K-H (Asp53, Tyr58, Lys84, and His117) and putative cofactor binding sites at Asp53, Ser147, Asn148, Gln169, Glu249, and Asn254
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?
additional information
?
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the recombinant enzyme exhibits broad substrate specificity towards various keto esters, ketones and aldehydes, detailed overview
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?
additional information
?
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gene contains the conserved catalytic tetrad D-Y-K-H (Asp53, Tyr58, Lys84, and His117) and putative cofactor binding sites at Asp53, Ser147, Asn148, Gln169, Glu249, and Asn254
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