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(R)-1-phenylethanol + NAD+
1-phenylethanone + NADH + H+
(R)-2-butanol + NAD+
2-butanone + NADH + H+
-
6% of the activity with (RS)-2-hexanol
-
-
r
(R)-2-hexanol + NAD+
2-hexanone + NADH + H+
-
30% of the activity with (RS)-2-hexanol
-
-
r
(R)-2-pentanol + NAD+
2-pentanone + NADH + H+
-
15% of the activity with (RS)-2-hexanol
-
-
r
(R)-3-butyn-2-ol + NAD+
but-3-yn-2-one + NADH + H+
-
0.5% of the activity with (RS)-2-hexanol
-
-
r
(R)-3-pentyn-2-ol + NAD+
pent-3-yn-2-one + NADH + H+
-
5.6% of the activity with (RS)-2-hexanol
-
-
r
(R)-3-phenyl-1-indanol + NADH + H+
(R)-3-phenyl-1-indanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
(S)-1,3-butanediol + NAD+ + H+
4-hydroxy-2-butanone + NADH
-
-
enantioselective oxidation of the (S)-isomer
-
?
(S)-1-phenyl 2-propanol + NADP+
phenylacetone + NADPH + H+
-
-
-
-
?
(S)-1-phenylethanol + NAD+
1 phenylethanone + NADH + H+
-
99% ethanoselective reaction
-
-
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
(S)-1-[4-(1-hydroxyethyl)phenyl]-methylketone + NADH + H+
(S)-1-(4-(1-hydroxy-ethyl)-phenyl)-ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
(S)-2-butanol + NAD+
2-butanone + NADH + H+
(S)-2-hexanol + NAD+
2-hexanone + NADH + H+
(S)-2-pentanol + NAD+
2-pentanone + NADH + H+
(S)-3-butyn-2-ol + NAD+
but-3-yn-2-one + NADH + H+
-
6.9% of the activity with (RS)-2-hexanol
-
-
r
(S)-3-pentyn-2-ol + NAD+
pent-3-yn-2-one + NADH + H+
-
33% of the activity with (RS)-2-hexanol
-
-
r
(S)-3-phenyl-1-indanone + NADH + H+
(S)-3-phenyl-1-indanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
(S)-alpha-tetralol + NAD+
alpha-tetralone + NADH + H+
-
99% ethanoselective reaction
-
-
r
1-(3-fluorophenyl)ethan-1-ol + NADP+
1-(3-fluorophenyl)ethan-1-one + NADPH + H+
-
-
-
-
?
1-(3-methoxyphenyl)propan-2-ol + NADP+
1-(3-methoxyphenyl)propan-2-one + NADPH + H+
-
-
-
-
?
1-(3-methylphenyl)ethan-1-ol + NADP+
1-(3-methylphenyl)ethan-1-one + NADPH + H+
-
-
-
-
?
1-(4-fluorophenyl)ethan-1-ol + NADP+
1-(4-fluorophenyl)ethan-1-one + NADPH + H+
-
-
-
-
?
1-(4-fluorophenyl)propan-2-ol + NADP+
1-(4-fluorophenyl)propan-2-one + NADPH + H+
-
-
-
-
?
1-(4-methylphenyl)ethan-1-ol + NADP+
1-(4-methylphenyl)ethan-1-one + NADPH + H+
-
-
-
-
?
1-(4-methylphenyl)propan-2-ol + NADP+
1-(4-methylphenyl)propan-2-one + NADPH + H+
-
-
-
-
?
1-(furan-2-yl)methylketone + NADH + H+
(S)-1-(furan-2-yl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
1-chloroacetophenone + NADH + H+
(1S)-2-chloro-1-phenylethanol + NAD+
-
-
more thasn 99% enantiomeric excess
-
?
1-hexanal + NADH + H+
hexan-1-ol + NAD+
-
254% of the activity with (RS)-2-hexanol
-
-
r
1-indanone + NADH + H+
(S)-1-indanol + NAD+
1-phenoxypropan-2-ol + NADP+
1-phenoxypropan-2-one + NADPH + H+
-
-
-
-
?
1-phenylbutan-1-one + NADH + H+
1-phenylbutan-1-ol + NAD+
1-phenylbutan-2-ol + NADP+
1-phenylbutan-2-one + NADPH + H+
-
-
-
-
?
1-phenylheptan-1-one + NADH + H+
1-phenylheptan-1-ol + NAD+
1-phenylhexan-1-one + NADH + H+
1-phenylhexan-1-ol + NAD+
1-phenylpentan-1-one + NADH + H+
1-phenylpentan-1-ol + NAD+
-
-
-
?
1-phenylpropan-1-one + NADH + H+
1-phenylpropan-1-ol + NAD+
-
-
-
?
1-phenylpropan-2-ol + NADP+
1-phenylpropan-2-one + NADPH + H+
-
-
-
-
?
1-tetralone + NADH + H+
(S)-1,2,3,4-tetrahydronaphthalen-1-ol + NAD+
-
100% (S)-enantiospecific product
-
-
r
2'-fluoroacetophenone + NADH + H+
(1S)-1-(2-fluorophenyl)ethanol + NAD+
2'-fluoroacetophenone + NADH + H+
(S)-1-(2-fluorophenyl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
2'-hydroxyacetophenone + NADH + H+
(S)-2-(1-hydroxyethyl)phenol + NAD+
-
100% (S)-enantiospecific product
-
-
r
2,2,2-trifluoroacetophenone + NADH + H+
(S)-1-phenyl-2,2,2-trifluoroethan-1-ol + NAD+
-
100% (S)-enantiospecific product
-
-
r
2,2,2-trifluoroacetophenone + NADH + H+
?
-
completely enantioselective reaction
-
-
r
2,2-dichloroacetophenone + NADH + H+
(S)-2,2-dichloro-1-phenylethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
2,2-difluoroacetophenone + NADH + H+
(S)-2,2-difluoro-1-phenylethan-1-ol + NAD+
-
100% (S)-enantiospecific product
-
-
r
2,3-butanedione + NADH + H+
? + NAD+
9% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
2,3-butanedione + NADPH + H+
? + NADP+
-
-
-
?
2,3-pentanedione + NADH + H+
? + NAD+
82% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
2,4'-dichloroacetophenone + NADH + H+
(S)-2-chloro-1-(4-chloro-phenyl)-ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
2-acetylpyridine + NADH + H+
(S)-1-(pyridin-2-yl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
2-acetylthiophene + NADH + H+
(S)-1-(thiophen-2-yl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
2-chloroacetophenone + NADH + H+
(R)-2-chloro-1-phenylethanol + NAD+
-
100% (R)-enantiospecific product
-
-
r
2-cyanoacetophenone + NADH + H+
(S)-3-hydroxy-3-phenylpropanenitrile + NAD+
-
100% (S)-enantiospecific product
-
-
r
2-decanone + NADH + H+
(S)-2-decanol + NAD+
-
159% of the activity with (RS)-2-hexanol
reaction is stereoselective
-
r
2-fluoroacetophenone + NADH + H+
(S)-2-fluoro-1-phenylethan-1-ol + NAD+
-
100% (S)-enantiospecific product
-
-
r
2-heptanone + NADH + H+
(S)-2-heptanol + NAD+
-
334% of the activity with (RS)-2-hexanol
reaction is stereoselective
-
r
2-hexanone + NADH + H+
(S)-2-hexanol + NAD+
-
225% of the activity with (RS)-2-hexanol
reaction is stereoselective
-
r
2-octanone + NADH + H+
(S)-2-octanol + NAD+
-
223% of the activity with (RS)-2-hexanol
reaction is stereoselective
-
r
3'-aminoacetophenone + NADH + H+
(S)-1-(3-aminophenyl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
3'-bromoacetophenone + NADH + H+
(S)-1-(3-bromophenyl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
3'-chloroacetophenone + NADH + H+
(S)-1-(3-chlorophenyl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
3'-fluoroacetophenone + NADH + H+
(1S)-1-(3-fluorophenyl)ethanol + NAD+
3'-fluoroacetophenone + NADH + H+
(S)-1-(3-fluorophenyl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
3'-hydroxyacetophenone + NADH + H+
(S)-3-[(1)-1-hydroxyethyl]phenol + NAD+
-
100% (S)-enantiospecific product
-
-
r
3'-methoxyacetophenone + NADH + H+
(S)-1-(3-methoxyphenyl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
3'-methylacetophenone + NADH + H+
(S)-1-(3-methylphenyl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
3-(3-bromo-phenyl)-3-oxo-propionic acid methyl ester + NADH + H+
(S)-methyl 3-(3-bromophenyl)-3-hydroxypropanoate + NAD+
-
100% (S)-enantiospecific product
-
-
r
3-(3-chloro-phenyl)-3-oxo-propionic acid methyl ester + NADH + H+
(S)-methyl 3-(3-chlorophenyl)-3-hydroxypropanoate + NAD+
-
100% (S)-enantiospecific product
-
-
r
3-(3-fluoro-phenyl)-3-oxo-propionic acid methyl ester + NADH + H+
(S)-methyl 3-(3-fluorophenyl)-3-hydroxypropanoate + NAD+
-
100% (S)-enantiospecific product
-
-
r
3-(3-methoxyphenyl)-3-oxo-propionic acid methylester + NADH + H+
(S)-methyl 3-hydroxy-3-(3-methoxyphenyl)propanoate + NAD+
-
100% (S)-enantiospecific product
-
-
r
3-(4-methoxy-phenyl)-3-oxo-propionic acid methyl ester + NADH + H+
(S)-methyl 3-hydroxy-3-(4-methoxyphenyl)propanoate + NAD+
-
100% (S)-enantiospecific product
-
-
r
3-acetylpyridine + NADH + H+
(S)-1-(pyridin-3-yl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
3-coumaranone + NADH + H+
(S)-2,3-dihydro-1-benzofuran-3-ol + NAD+
-
100% (S)-enantiospecific product
-
-
r
3-heptanone + NADH + H+
3-hexanol + NADH + H+
-
-
-
?
4'-acetoxy acetophenone + NADH + H+
(1S)-1-(4-acetoxyphenyl)ethanol + NAD+
4'-acetyl acetophenone + NADH + H+
(S)-1-(4-(1-hydroxy-ethyl)-phenyl)-ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
4'-acetyl pyridine + NADH + H+
(1S)-1-(pyridin-4-yl)ethanol + NAD+
4'-acetylbiphenyl + NADH + H+
(S)-1-(biphenyl-4-yl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
4'-acetylphenyl methanesulfonate + NADH + H+
(S)-4-(1-hydroxyethyl)phenyl methanesulfonate + NAD+
-
100% (S)-enantiospecific product
-
-
r
4'-aminoacetophenone + NADH + H+
(S)-1-(4-aminophenyl)ethanol + NAD+
-
50% (S)-enantiospecific product
-
-
r
4'-bromoacetophenone + NADH + H+
(1S)-1-(4-bromophenyl)ethanol + NAD+
4'-bromoacetophenone + NADH + H+
(S)-1-(4-bromophenyl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
4'-chloroacetophenone + NADH + H+
(1S)-1-(4-chlorophenyl)ethanol + NAD+
-
83% of the activity with acetophenone
-
-
?
4'-chloroacetophenone + NADH + H+
(S)-1-(4-chlorophenyl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
4'-ethylacetophenone + NADH + H+
(S)-1-(4-ethylphenyl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
4'-fluoroacetophenone + NADH + H+
(1S)-1-(4-fluorophenyl)ethanol + NAD+
-
117% of the activity with acetophenone
-
-
?
4'-fluoroacetophenone + NADH + H+
(S)-1-(4-fluorophenyl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
4'-hydroxyacetophenone + NADH + H+
(S)-4-(1-hydroxyethyl)phenol + NAD+
-
90% (S)-enantiospecific product
-
-
r
4'-iodoacetophenone + NADH + H+
(1S)-1-(4-iodophenyl)ethanol + NAD+
-
31% of the activity with acetophenone
-
-
?
4'-methoxyacetophenone + NADH + H+
(S)-1-(4-methoxyphenyl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
4'-nitroacetophenone + NADH + H+
(S)-1-(4-nitrophenyl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
4-acetylbenzonitrile + NADH + H+
(S)-4-(1-hydroxyethyl)benzonitrile + NAD+
-
100% (S)-enantiospecific product
-
-
r
4-acetylpyridine + NADH + H+
(S)-1-(pyridin-4-yl)ethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
4-chloro-3-oxobutanoate + NADH + H+
(S)-4-chloro-3-hydroxybutanoate + NAD+
-
99% enantiomeric excess of (S)-enantiomer
-
?
4-methylpentan-2-ol + NADP+
4-methylpentan-2-one + NADPH + H+
-
-
-
-
?
4-phenylbutan-2-ol + NADP+
4-phenylbutan-2-one + NADPH + H+
-
-
-
-
?
6-hydroxy-1-indanone + NADH + H+
(S)-2,3-dihydro-1H-indene-1,6-diol + NAD+
-
100% (S)-enantiospecific product
-
-
r
6-methyl-5-hepten-2-one + NADH + H+
(S)-6-methyl-5-hepten-2-ol + NAD+
-
-
188% of the activity with (RS)-2-hexanol
-
r
acetophenone + NADH + H+
(1S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
alpha-phenylethanol + NAD+
87% of the activity with phenylacetaldehyde
-
-
?
acetophenone + NADPH + H+
(1S)-1-phenylethanol + NADP+
-
-
-
?
alpha-tetralone + NADH + H+
(S)-alpha-tetralol + NAD+
-
completely enantioselective reaction
99% enantiomeric excess after 6 h at 50°C
-
r
capronaldehyde + NADH + H+
n-hexanol + NAD+
522% of the activity with phenylacetaldehyde
-
-
?
ethyl (R)-4-chloro-3-hydroxybutanoate + NAD+
ethyl 4-chloro-3-oxobutanoate + NADH + H+
-
-
38.1% of the activity with (RS)-2-hexanol
-
r
ethyl 2-chloro-3-oxobutanoate + NADH + H+
ethyl 2-chloro-3-hydroxybutanoate + NAD+
49% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
ethyl 3-oxobutanoate + NADH + H+
ethyl 3-hydroxybutanoate + NAD+
28% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
ethyl 3-oxobutanoate + NADPH + H+
ethyl (S)-3-hydroxybutanoate + NADP+
-
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADH + H+
ethyl (R)-4-chloro-3-hydroxybutanoate + NAD+
ethyl 4-chloro-3-oxobutanoate + NADH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NAD+
-
product in more than 99% enantiomeric excess
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
heptan-1-ol + NADP+
heptanal + NADPH + H+
-
-
-
-
?
heptan-2-ol + NADP+
heptan-2-one + NADPH + H+
-
-
-
-
?
heptan-2-one + NADH + H+
heptan-2-ol + NAD+
-
-
-
?
heptan-3-one + NADH + H+
heptan-3-ol + NAD+
-
-
-
?
heptan-4-one + NADH + H+
heptan-4-ol + NAD+
-
-
-
?
hexan-1-ol + NADP+
hexanal + NADPH + H+
-
-
-
-
?
hexan-2-ol + NADP+
hexan-2-one + NADPH + H+
-
-
-
-
?
hexan-2-one + NADH + H+
hexan-2-ol + NAD+
-
-
-
?
hexan-3-one + NADH + H+
hexan-3-ol + NAD+
-
-
-
?
methyl (4-chlorobenzoyl)acetate + NADH + H+
(S)-methyl 3-(4-chlorophenyl)-3-hydroxypropanoate + NAD+
-
100% (S)-enantiospecific product
-
-
r
methyl 3-(4-ethylphenyl)-3-oxopropanoate + NADH + H+
(S)-methyl 3-(4-ethylphenyl)-3-hydroxypropanoate + NAD+
-
100% (S)-enantiospecific product
-
-
r
methyl 3-(4-methylphenyl)-3-oxopropanoate + NADH + H+
(S)-methyl 3-hydroxy-3-(4-methylphenyl)propanoate + NAD+
-
100% (S)-enantiospecific product
-
-
r
methyl 3-oxo-3-phenylpropanoate + NADH + H+
(S)-methyl 3-hydroxy-3-phenylpropanoate + NAD+
-
100% (S)-enantiospecific product
-
-
r
methyl 4-bromobenzoylacetate + NADH + H+
(S)-methyl 3-(4-bromophenyl)-3-hydroxypropanoate + NAD+
-
100% (S)-enantiospecific product
-
-
r
methyl 4-chloro-3-oxobutanoate + NADPH + H+
methyl (S)-4-chloro-3-hydroxybutanoate + NADP+
-
-
-
?
methyl 4-fluorobenzoylacetate + NADH + H+
(S)-methyl 3-(4-fluorophenyl)-3-hydroxypropanoate + NAD+
-
100% (S)-enantiospecific product
-
-
r
n-valeraldehyde + NADH + H+
? + NAD+
-
84% of the activity with (RS)-2-hexanol
-
-
r
nonan-2-one + NADH + H+
nonan-2-ol + NAD+
-
-
-
?
nonan-3-one + NADH + H+
nonan-3-ol + NAD+
-
-
-
?
nonan-4-one + NADH + H+
nonan-4-ol + NAD+
-
-
-
?
nonan-5-one + NADH + H+
nonan-5-ol + NAD+
-
-
-
?
octan-1-ol + NADP+
octanal + NADPH + H+
-
-
-
-
?
octan-2-ol + NADP+
octan-2-one + NADPH + H+
-
-
-
-
?
octan-2-one + NADH + H+
octan-2-ol + NAD+
octan-3-one + NADH + H+
octan-3-ol + NAD+
-
-
-
?
octan-4-one + NADH + H+
octan-4-ol + NAD+
-
-
-
?
p-chloro-acetophenone + NADH + H+
alpha-(p-chlorophenyl)ethanol + NAD+
288% of the activity with phenylacetaldehyde
-
-
?
pentan-1-ol + NADP+
pentanal + NADPH + H+
-
-
-
-
?
pentan-2-ol + NADP+
pentan-2-one + NADPH + H+
-
-
-
-
?
pentan-2-one + NADH + H+
pentan-2-ol + NAD+
-
-
-
?
pentan-3-one + NADH + H+
pentan-3-ol + NAD+
-
-
-
?
phenylacetaldehyde + NADH + H+
2-phenylethanol + NAD+
-
-
-
?
propiophenone + NADH + H+
(S)-1-phenylpropan-1-ol + NAD+
-
100% (S)-enantiospecific product
-
-
r
pyruvic acid ethyl ester + NADH + H+
? + NAD+
-
225% of the activity with (RS)-2-hexanol
-
-
r
rac-1-indanol + NAD+
1-indanone + NADH + H+
-
3900% activity compared to (S)-1-phenylethanol
-
-
r
rac-alpha-tetralol + NAD+
alpha-tetralone + NADH + H+
-
2700% activity compared to (S)-1-phenylethanol
-
-
r
valeraldehyde + NADH + H+
n-pentanol + NAD+
433% of the activity with phenylacetaldehyde
-
-
?
additional information
?
-
(R)-1-phenylethanol + NAD+
1-phenylethanone + NADH + H+
-
0.9% of the activity with (RS)-2-hexanol
-
-
r
(R)-1-phenylethanol + NAD+
1-phenylethanone + NADH + H+
-
21% of the activity with (RS)-2-hexanol
-
-
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
-
-
-
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
the enzyme catalyzes the stereospecific oxidation of (S)-1-phenylethanol to acetophenone during anaerobic ethylbenzene mineralization, but also the reverse reaction, i.e. NADH-dependent enantioselective reduction of acetophenone to (S)-1-phenylethanol, high enantioselectivity of the reaction
-
-
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
-
-
-
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
the enzyme catalyzes the stereospecific oxidation of (S)-1-phenylethanol to acetophenone during anaerobic ethylbenzene mineralization, but also the reverse reaction, i.e. NADH-dependent enantioselective reduction of acetophenone to (S)-1-phenylethanol, high enantioselectivity of the reaction
-
-
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
-
-
-
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
-
-
-
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
activity of the wild-type enzyme, the mutant I886A is (R)-specific forming (R)-1-phenylethanol
-
-
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
-
-
-
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
asymmetric reduction of acetophenone to produce (S)-1-phenylethanol, with an enantiomeric excess of more than 99%
-
-
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
-
-
-
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
asymmetric reduction of acetophenone to produce (S)-1-phenylethanol, with an enantiomeric excess of more than 99%
-
-
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
-
-
-
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
-
-
-
r
(S)-2-butanol + NAD+
2-butanone + NADH + H+
-
27% of the activity with (RS)-2-hexanol
-
-
r
(S)-2-butanol + NAD+
2-butanone + NADH + H+
-
-
-
-
r
(S)-2-butanol + NAD+
2-butanone + NADH + H+
-
-
-
-
?
(S)-2-butanol + NAD+
2-butanone + NADH + H+
-
-
-
-
?
(S)-2-butanol + NAD+
2-butanone + NADH + H+
-
-
-
-
?
(S)-2-hexanol + NAD+
2-hexanone + NADH + H+
-
121% of the activity with (RS)-2-hexanol
-
-
r
(S)-2-hexanol + NAD+
2-hexanone + NADH + H+
-
reaction is stereoselective
-
-
r
(S)-2-pentanol + NAD+
2-pentanone + NADH + H+
-
91% of the activity with (RS)-2-hexanol
-
-
r
(S)-2-pentanol + NAD+
2-pentanone + NADH + H+
-
-
-
-
r
1-indanone + NADH + H+
(S)-1-indanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
1-indanone + NADH + H+
(S)-1-indanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
1-indanone + NADH + H+
(S)-1-indanol + NAD+
-
-
99% enantiomeric excess after 6 h at 50°C
-
?
1-phenylbutan-1-one + NADH + H+
1-phenylbutan-1-ol + NAD+
-
-
-
?
1-phenylbutan-1-one + NADH + H+
1-phenylbutan-1-ol + NAD+
-
-
-
?
1-phenylheptan-1-one + NADH + H+
1-phenylheptan-1-ol + NAD+
-
-
-
?
1-phenylheptan-1-one + NADH + H+
1-phenylheptan-1-ol + NAD+
-
-
-
?
1-phenylhexan-1-one + NADH + H+
1-phenylhexan-1-ol + NAD+
-
-
-
?
1-phenylhexan-1-one + NADH + H+
1-phenylhexan-1-ol + NAD+
-
-
-
?
2'-fluoroacetophenone + NADH + H+
(1S)-1-(2-fluorophenyl)ethanol + NAD+
-
102% of the activity with acetophenone
-
-
?
2'-fluoroacetophenone + NADH + H+
(1S)-1-(2-fluorophenyl)ethanol + NAD+
-
102% of the activity with acetophenone
-
-
?
3'-fluoroacetophenone + NADH + H+
(1S)-1-(3-fluorophenyl)ethanol + NAD+
-
102% of the activity with acetophenone
-
-
?
3'-fluoroacetophenone + NADH + H+
(1S)-1-(3-fluorophenyl)ethanol + NAD+
-
102% of the activity with acetophenone
-
-
?
4'-acetoxy acetophenone + NADH + H+
(1S)-1-(4-acetoxyphenyl)ethanol + NAD+
-
80% of the activity with acetophenone
-
-
?
4'-acetoxy acetophenone + NADH + H+
(1S)-1-(4-acetoxyphenyl)ethanol + NAD+
-
80% of the activity with acetophenone
-
-
?
4'-acetyl pyridine + NADH + H+
(1S)-1-(pyridin-4-yl)ethanol + NAD+
-
98% of the activity with acetophenone
102% of the activity with acetophenone, enantiomeric excess of more than 99% for (S)-configuration of product
-
?
4'-acetyl pyridine + NADH + H+
(1S)-1-(pyridin-4-yl)ethanol + NAD+
-
98% of the activity with acetophenone
102% of the activity with acetophenone, enantiomeric excess of more than 99% for (S)-configuration of product
-
?
4'-bromoacetophenone + NADH + H+
(1S)-1-(4-bromophenyl)ethanol + NAD+
-
82% of the activity with acetophenone
-
-
?
4'-bromoacetophenone + NADH + H+
(1S)-1-(4-bromophenyl)ethanol + NAD+
-
82% of the activity with acetophenone
-
-
?
acetophenone + NADH + H+
(1S)-1-phenylethanol + NAD+
-
-
enantiomeric excess of more than 99% for (S)-configuration of product
-
?
acetophenone + NADH + H+
(1S)-1-phenylethanol + NAD+
-
-
-
?
acetophenone + NADH + H+
(1S)-1-phenylethanol + NAD+
-
-
-
?
acetophenone + NADH + H+
(1S)-1-phenylethanol + NAD+
-
-
-
-
?
acetophenone + NADH + H+
(S)-1-phenylethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
acetophenone + NADH + H+
(S)-1-phenylethanol + NAD+
-
100% (S)-enantiospecific product
-
-
r
acetophenone + NADH + H+
(S)-1-phenylethanol + NAD+
-
completely enantioselective reaction
99% enantiomeric excess after 6 h at 50°C
-
r
acetophenone + NADH + H+
(S)-1-phenylethanol + NAD+
-
-
-
-
r
acetophenone + NADH + H+
(S)-1-phenylethanol + NAD+
-
-
-
-
r
ethyl 4-chloro-3-oxobutanoate + NADH + H+
ethyl (R)-4-chloro-3-hydroxybutanoate + NAD+
-
-
-
-
r
ethyl 4-chloro-3-oxobutanoate + NADH + H+
ethyl (R)-4-chloro-3-hydroxybutanoate + NAD+
-
-
-
-
r
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
-
the enzyme catalyzes the asymmetric reduction of ethyl 4-chloro-3-oxobutanoate, 99% enantiomeric excess
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
-
the enzyme catalyzes the asymmetric reduction of ethyl 4-chloro-3-oxobutanoate, 99% enantiomeric excess
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
-
-
-
?
octan-2-one + NADH + H+
octan-2-ol + NAD+
-
-
-
?
octan-2-one + NADH + H+
octan-2-ol + NAD+
-
-
-
?
additional information
?
-
-
application of PEDH for asymmetric reduction of 42 prochiral ketones and 11 beta-keto esters to enantiopure secondary alcohols, high enantioselectivity of the reaction, substrate binding mechanism analysis by molecular docking, modeling of enzyme-substrate complexes, overview
-
-
?
additional information
?
-
-
application of PEDH for asymmetric reduction of 42 prochiral ketones and 11 beta-keto esters to enantiopure secondary alcohols, high enantioselectivity of the reaction, substrate binding mechanism analysis by molecular docking, modeling of enzyme-substrate complexes, overview
-
-
?
additional information
?
-
no substrates: cetophenone, 2-hydroxyacetophenone, acetone, butanone, 2-pentanone, 3-pentanone, 2-hexanone, 2-heptanone, 2-octanone, cyclohexanone, acetylacetone, 2,5-hexanedione and 5,5-dimethyl-l,3-cyclohexanedione
-
-
?
additional information
?
-
-
primary alcohols are not accepted as substrate
-
-
?
additional information
?
-
-
the enzyme catalyzes stereoselective oxidation of (S)-secondary alcohols to corresponding ketones
-
-
?
additional information
?
-
-
the enzyme catalyzes stereoselective oxidation of (S)-secondary alcohols to corresponding ketones
-
-
?
additional information
?
-
-
substrate specificity of ADHTt in the oxidation and the reduction reactions depends on the substrate, cf. (R)-specific secondary alcohol dehydrogenase, detailed overview. The enzyme shows a high reduction rate with halogenated aryl ketones, such as 2,2,2-trifluoroacetophenone, 2-chloroacetophenone, and 4-chlorobutyrophenone, and with aryl diketones, such as 1-phenyl-1,2-propanedione, although it is not active on benzil, i.e. diphenylethanedione. ADHTt proves to be very effective in reducing aryl alpha-keto esters, although it is not active on aliphatic alpha-keto esters and aryl beta-keto ester. Critical role of the D37 residue in discriminating NAD(H) from NADP(H)
-
-
?
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-
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-
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-
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-
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