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Information on EC 1.1.1.B4 - (R)-specific secondary alcohol dehydrogenase (NADH)
for references in articles please use BRENDA:EC1.1.1.B4
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preliminary BRENDA-supplied EC number
EC Tree 1 Oxidoreductases
1.1 Acting on the CH-OH group of donors
1.1.1 With NAD+ or NADP+ as acceptor
1.1.1.B4 (R)-specific secondary alcohol dehydrogenase (NADH)
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
showSynonyms
secondary alcohol dehydrogenase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
ADH1
carbonyl reductase
carbonyl reductase (NADH, specific for (S)-configuration of alcohol)
CHY1186
CpCR
mLDH
SDR
additional information
additional information
-
the enzyme belongs to the short-chain dehydrogenase/reductase, SDR, superfamily
additional information
Thermus thermophilus HB27 / ATCC BAA-163 / DSM 7039
-
the enzyme belongs to the short-chain dehydrogenase/reductase, SDR, superfamily
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(R)-R-CHOH-R' + NAD+ = R-CO-R' + NADH + H+
kinetic mechanism is ordered bi-bi with the cofactor binding first and releasing last. The enzyme transfers the pro-R hydride of NADH to the si face of carbonyl compounds to yield (R)-alcohols
-
(R)-R-CHOH-R' + NAD+ = R-CO-R' + NADH + H+
kinetic mechanism is ordered bi-bi with the cofactor binding first and releasing last. The enzyme transfers the pro-R hydride of NADH to the si face of carbonyl compounds to yield (R)-alcohols
-
-
(R)-R-CHOH-R' + NAD+ = R-CO-R' + NADH + H+
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
secondary alcohol:NAD+ oxidoreductase (specific for (R)-configuration of alcohol)
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(R)-(trifluoromethyl)benzyl alcohol + NADH + H+
?
-
Substrates: 93% ethanoselective reaction
Products: -
Products: -
r
(R)-2-pentanol + NAD+
2-pentanone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
1,2-butanediol + NAD+
? + NADH
-
Substrates: 20% of the activity with 2-propanol
Products: -
Products: -
r
1,2-propanediol + NAD+
? + NADH
-
Substrates: 45% of the activity with 2-propanol
Products: -
Products: -
r
1,3-butanediol + NAD+
? + NADH
-
Substrates: 126% of the activity with 2-propanol
Products: -
Products: -
r
1-(2-pyridyl)acetone + NADPH + H+
1-(2-pyridyl)ethanol + NADP+
-
Substrates: -
Products: -
Products: -
r
1-(2-thienyl)acetone + NADPH + H+
1-(2-thienyl)ethanol + NADP+
-
Substrates: -
Products: -
Products: -
r
1-(3-pyridyl)acetone + NADPH + H+
1-(3-pyridyl)ethanol + NADP+
-
Substrates: -
Products: -
Products: -
r
1-(3-thienyl)acetone + NADPH + H+
1-(3-thienyl)ethanol + NADP+
-
Substrates: -
Products: -
Products: -
r
1-(4-pyridyl)acetone + NADPH + H+
1-(4-pyridyl)ethanol + NADP+
-
Substrates: -
Products: -
Products: -
r
1-phenylpropanone + NADPH + H+
1-phenylpropanol + NADP+
-
Substrates: -
Products: -
Products: -
r
1-propanol + NAD+
propanal + NADH
-
Substrates: 9% of the activity with 2-propanol
Products: -
Products: -
r
2',4'-difluoro-acetophenone + NADPH + H+
1-(2',4'-difluoro)-phenylethanol + NADP+
-
Substrates: -
Products: -
Products: -
r
2'-methylacetophenone + NADPH + H+
1-(2'-methyl)phenylethanol + NADP+
-
Substrates: -
Products: -
Products: -
r
2,2,2-trifluoro-1-phenylethanone + NADH + H+
(1R)-2,2,2-trifluoro-1-phenylethanol + NAD+
-
Substrates: -
Products: 21% of the activity with 1-phenylpropane-1,2-dione
Products: 21% of the activity with 1-phenylpropane-1,2-dione
r
2,2,2-trifluoro-1-phenylethanone + NADH + H+
(1S)-2,2,2-trifluoro-1-phenylethanol + NAD+
-
Substrates: -
Products: 37% yield, 92% enantiomeric excess
Products: 37% yield, 92% enantiomeric excess
?
2,2,2-trifluoroacetophenone + NADH + H+
(1R)-2,2,2-trifluoro-1-phenylethanol + NAD+
-
Substrates: completely enantioselective reaction
Products: -
Products: -
r
2,3-pentanedione + NADPH + H+
(R)-2-hydroxy-3-oxo-pentane + NADP+
-
Substrates: -
Products: -
Products: -
?
2-amino-3',4'-dihydroxyacetophenone + NADH + H+
? + NAD+
-
Substrates: -
Products: -
Products: -
r
2-amino-4'-amino-acetophenone + NADH + H+
? + NAD+
-
Substrates: -
Products: -
Products: -
r
2-amino-4'-hydroxyacetophenone + NADH + H+
? + NAD+
-
Substrates: -
Products: -
Products: -
r
2-amino-acetophenone + NADH + H+
(R)-2-amino-1-phenylethanol + NAD+
-
Substrates: -
Products: -
Products: -
r
2-butanol + NAD+
2-butanone + NADH
-
Substrates: (R)-isomer is preferred over (S)-isomer
Products: -
Products: -
r
2-butanone + NAD+
2-butanol + NADH + H+
-
Substrates: 274% of the activity with beta-hydroxyacetophenone
Products: -
Products: -
?
2-butanone + NADH
2-butanol + NAD+
-
Substrates: 83% of the activity with acetone
Products: -
Products: -
r
2-heptanone + NAD+
2-heptanol + NADH + H+
-
Substrates: 281% of the activity with beta-hydroxyacetophenone
Products: -
Products: -
?
2-hexanone + NAD+
2-hexanol + NADH + H+
-
Substrates: 259% of the activity with beta-hydroxyacetophenone
Products: -
Products: -
?
2-octanone + NAD+
2-octanol + NADH + H+
-
Substrates: 350% of the activity with beta-hydroxyacetophenone
Products: -
Products: -
?
2-pentanone + NAD+
2-pentanol + NADH + H+
-
Substrates: 249% of the activity with beta-hydroxyacetophenone
Products: -
Products: -
?
2-pentanone + NADH + H+
(S)-2-hydroxypentane + NAD+
-
Substrates: 6% of the activity with 2-butanone
Products: -
Products: -
r
2-pentanone + NADH + H+
2-pentanol + NAD+
-
Substrates: 44% of the activity with acetone
Products: -
Products: -
r
3'-bromo-acetophenone + NADPH + H+
1-(3'-bromo-)phenylethanol + NADP+
-
Substrates: -
Products: -
Products: -
r
3'-chloroacetophenone + NADPH + H+
1-(3'-chlorophenyl)ethanol + NADP+
-
Substrates: -
Products: -
Products: -
r
3'-iodoacetophenone + NADPH + H+
1-(3'-iodophenyl)ethanol + NADP+
-
Substrates: -
Products: -
Products: -
r
3'-methoxyacetophenone + NADPH + H+
1-(3'-methoxyphenyl)ethanol + NADP+
-
Substrates: -
Products: -
Products: -
r
3'-methylacetophenone + NADPH + H+
1-(3'-methylphenyl)ethanol + NADP+
-
Substrates: -
Products: -
Products: -
r
3'-trifluoromethyl-acetophenone + NADPH + H+
1-[(3'-trifluoromethyl)phenyl]ethanol + NADP+
-
Substrates: -
Products: -
Products: -
r
3'-trifluoromethylacetophenone + NADPH + H+
1-[(3'-trifluoromethyl)phenyl]ethanol + NADP+
-
Substrates: -
Products: -
Products: -
r
3,5-bis(trifluoromethyl)acetophenone + NADH + H+
(R)-[3,5-bis(trifluoromethyl)phenyl]ethanol + NAD+
3-(dimethylamino)-1-phenylpropan-1-one + NADH
(1S)-3-dimethylamino-1-phenylpropan-1-ol + NAD+
-
Substrates: -
Products: 24% of the activity with 1-phenylpropane-1,2-dione
Products: 24% of the activity with 1-phenylpropane-1,2-dione
r
3-chloro-pentane-2,4-dione + NADH
(4R)-3-chloro-4-hydroxypentan-2-one + NAD+
-
Substrates: 336% of the activity with 2-butanone
Products: -
Products: -
r
3-hexanone + NAD+
3-hexanol + NADH + H+
-
Substrates: 29% of the activity with beta-hydroxyacetophenone
Products: -
Products: -
?
3-pentanol + NAD+
3-pentanone + NADH
-
Substrates: 23% of the activity with 2-propanol
Products: -
Products: -
r
3-pentanone + NAD+
3-pentanol + NADH + H+
-
Substrates: 35% of the activity with beta-hydroxyacetophenone
Products: -
Products: -
?
3-pentanone + NADH
3-pentanol + NAD+
-
Substrates: 16% of the activity with acetone
Products: -
Products: -
r
4-hydroxy-2-butanone + NADH
? + NAD+
-
Substrates: 95% of the activity with acetone
Products: -
Products: -
r
4-phenylbutan-2-one + NADH
(2R)-4-phenylbutan-2-ol + NAD+
-
Substrates: -
Products: 18% of the activity with 1-phenylpropane-1,2-dione
Products: 18% of the activity with 1-phenylpropane-1,2-dione
r
4-phenylbutan-2-one + NADPH + H+
(2R)-4-phenylbutan-2-ol + NADP+
-
Substrates: -
Products: 99% conversion, 97.9% enantiomeric excess
Products: 99% conversion, 97.9% enantiomeric excess
?
5-chloropentan-2-one + NADH
(2S)-5-chloropentan-2-ol + NAD+
-
Substrates: -
Products: 48% yield, 93% enantiomeric excess
Products: 48% yield, 93% enantiomeric excess
?
6-methylhept-5-en-2-one + NADH
(2S)-6-methylhept-5-en-2-ol + NAD+
-
Substrates: -
Products: 51% yield, 97% enantiomeric excess
Products: 51% yield, 97% enantiomeric excess
?
acetone + NAD+
isopropanol + NADH + H+
-
Substrates: 260% of the activity with beta-hydroxyacetophenone
Products: -
Products: -
?
acetone + NADPH + H+
2-propanol + NADP+
-
Substrates: -
Products: -
Products: -
r
acetophenone + NADH + H+
1-phenylethanol + NAD+
-
Substrates: -
Products: -
Products: -
r
acetophenone + NADPH + H+
(1R)-1-phenylethanol + NADP+
Substrates: -
Products: -
Products: -
?
acetophenone + NADPH + H+
1-phenylethanol + NADP+
-
Substrates: -
Products: -
Products: -
r
acetophenone + NADPH + H+
phenylethanol + NADP+
-
Substrates: -
Products: -
Products: -
?
adrenalone + NADH + H+
(R)-epinephrine + NAD+
-
Substrates: the NAD(H)-dependent dehydrogenase catalyzes the asymmetric reduction of adrenalone (corticosterone) to (R)-epinephrine, with an enantiomeric excess (e.e value) of more than 99%
Products: -
Products: -
r
beta-hydroxyacetophenone + NAD+
(R)-1-phenyl-1,2-ethanediol + NADH + H+
-
Substrates: -
Products: formation of (R)-enantiomner with 100% enantiomeric excess
Products: formation of (R)-enantiomner with 100% enantiomeric excess
?
ephedrine + NAD+
1-(3,4-dihydroxyphenyl)-2-(methylamino)-propan-1-one + NADH + H+
-
Substrates: -
Products: -
Products: -
r
ethyl (R)-mandelate + NADH + H+
ethyl benzoylformate + NAD+
-
Substrates: 95% ethanoselective reaction
Products: -
Products: -
r
ethyl 2-oxo-3-phenylpropanoate + NADH + H+
ethyl 2-hydroxy-3-phenylpropanoate + NAD+
Substrates: 48% of the activity with ethyl 2-oxopropanoate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
?
ethyl 2-oxo-4-phenylbutanoate + NADH + H+
ethyl 2-hydroxy-4-phenylbutanoate + NAD+
Substrates: 135% of the activity with ethyl 2-oxopropanoate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
?
ethyl 2-oxopropanoate + NADH + H+
ethyl 2-hydroxypropanoate + NAD+
Substrates: -
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
?
ethyl 3-oxohexanoate + NADH + H+
ethyl 3-hydroxyhexanoate + NAD+
Substrates: 105% of the activity with ethyl 2-oxopropanoate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
?
ethyl oxo(phenyl)acetate + NADH + H+
ethyl hydroxy(phenyl)acetate + NAD+
Substrates: 270% of the activity with ethyl 2-oxopropanoate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
?
ethyl oxo(phenyl)acetate + NADPH + H+
ethyl (2S)-hydroxy(phenyl)acetate + NADP+
-
Substrates: -
Products: -
Products: -
?
hydroxyacetone + NADH
? + NAD+
-
Substrates: 92% of the activity with acetone
Products: -
Products: -
r
isoproterenol + NAD+
1-(3,4-dihydroxyphenyl)-2-[(propan-2-yl)amino]ethane-1-one + NADH + H+
-
Substrates: -
Products: -
Products: -
r
methyl (R)-mandelate + NADH + H+
methyl benzoylformate + NAD+
-
Substrates: 92% ethanoselective reaction
Products: -
Products: -
r
methyl 3-oxobutanoate + NADH
methyl (3S)-3-hydroxybutanoate + NAD+
-
Substrates: 135% of the activity with 2-butanone
Products: -
Products: -
r
methyl benzoylformate + NADH + H+
methyl (R)-mandelate + NAD+
-
Substrates: completely enantioselective reaction
Products: 92% enantiomeric excess after 6 h at 50Ā°C
Products: 92% enantiomeric excess after 6 h at 50Ā°C
r
methyl oxo(phenyl)acetate + NADH
methyl (2S)-hydroxy(phenyl)ethanoate + NAD+
-
Substrates: -
Products: 79% yield, 98% enantiomeric excess
Products: 79% yield, 98% enantiomeric excess
?
methylpyruvate + NADH
? + NAD+
-
Substrates: 64% of the activity with acetone
Products: -
Products: -
r
pentane-2,4-dione + NADH
(4R)-4-hydroxypentan-2-one + NAD+
-
Substrates: 32% of the activity with 2-butanone
Products: -
Products: -
r
phenylephrine + NAD+
1-(3-hydroxyphenyl)-2-(methylamino)ethane-1-one + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(R)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(R)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(R)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
?
(R)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
?
(R)-1-phenylethanol + NAD+
acetophenone + NADH + H+
Substrates: activity of mutant I886A, the wild-type enzyme is (S)-specific forming (S)-1-phenylethanol
Products: -
Products: -
r
(R)-2-butanol + NAD+
2-butanone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(R)-2-butanol + NAD+
2-butanone + NADH + H+
-
Substrates: -
Products: -
Products: -
?
(R)-2-butanol + NAD+
2-butanone + NADH + H+
-
Substrates: -
Products: -
Products: -
?
(R)-2-butanol + NAD+
2-butanone + NADH + H+
-
Substrates: -
Products: -
Products: -
?
1-(2-phenylcyclopropyl)ethanone + NADH
(1R)-1-(2-phenylcyclopropyl)ethanol + NAD+
-
Substrates: -
Products: 18% of the activity with 1-phenylpropane-1,2-dione
Products: 18% of the activity with 1-phenylpropane-1,2-dione
r
1-(2-phenylcyclopropyl)ethanone + NADH
(1R)-1-(2-phenylcyclopropyl)ethanol + NAD+
-
Substrates: -
Products: 18% of the activity with 1-phenylpropane-1,2-dione
Products: 18% of the activity with 1-phenylpropane-1,2-dione
r
1-butanol + NAD+
butanal + NADH
-
Substrates: 11% of the activity with 2-propanol
Products: -
Products: -
r
1-butanol + NAD+
butanal + NADH
-
Substrates: 11% of the activity with 2-propanol
Products: -
Products: -
r
1-chloropentane-2,4-dione + NADH
(4R)-5-chloro-4-hydroxypentan-2-one + NAD+
-
Substrates: -
Products: 76% yield, 98% enantiomeric excess
Products: 76% yield, 98% enantiomeric excess
?
1-chloropentane-2,4-dione + NADH
(4R)-5-chloro-4-hydroxypentan-2-one + NAD+
-
Substrates: -
Products: 76% yield, 98% enantiomeric excess
Products: 76% yield, 98% enantiomeric excess
?
1-phenoxypropan-2-one + NADH
(2R)-1-phenoxypropan-2-ol + NAD+
-
Substrates: -
Products: 21% of the activity with 1-phenylpropane-1,2-dione
Products: 21% of the activity with 1-phenylpropane-1,2-dione
r
1-phenoxypropan-2-one + NADH
(2R)-1-phenoxypropan-2-ol + NAD+
-
Substrates: -
Products: 21% of the activity with 1-phenylpropane-1,2-dione
Products: 21% of the activity with 1-phenylpropane-1,2-dione
r
1-phenyl-1,2-propandione + NADPH + H+
? + NADP+
-
Substrates: -
Products: -
Products: -
?
1-phenyl-1,2-propandione + NADPH + H+
? + NADP+
-
Substrates: -
Products: -
Products: -
?
1-phenylethanone + NADH
(1R)-1-phenylethanol + NAD+
-
Substrates: -
Products: 34% yield, 94% enantiomeric excess
Products: 34% yield, 94% enantiomeric excess
?
1-phenylethanone + NADH
(1R)-1-phenylethanol + NAD+
-
Substrates: -
Products: 34% yield, 94% enantiomeric excess
Products: 34% yield, 94% enantiomeric excess
?
1-phenylpropane-1,2-dione + NADH
(1S)-1-hydroxy-1-phenylpropan-2-one + NAD+
-
Substrates: -
Products: 83% yield, 86% enantiomeric excess
Products: 83% yield, 86% enantiomeric excess
?
1-phenylpropane-1,2-dione + NADH
(1S)-1-hydroxy-1-phenylpropan-2-one + NAD+
-
Substrates: -
Products: 83% yield, 86% enantiomeric excess
Products: 83% yield, 86% enantiomeric excess
?
2,3-butanediol + NAD+
? + NADH
-
Substrates: 73% of the activity with 2-propanol
Products: -
Products: -
r
2,3-butanediol + NAD+
? + NADH
-
Substrates: 73% of the activity with 2-propanol
Products: -
Products: -
r
2,3-butanedione + NADPH + H+
(R)-2-hydroxy-3-oxo-butane + NADP+
-
Substrates: -
Products: -
Products: -
?
2,3-butanedione + NADPH + H+
(R)-2-hydroxy-3-oxo-butane + NADP+
-
Substrates: -
Products: -
Products: -
?
2-pentanol + NAD+
2-pentanone + NADH
-
Substrates: 46% of the activity with 2-propanol
Products: -
Products: -
r
2-pentanol + NAD+
2-pentanone + NADH
-
Substrates: 46% of the activity with 2-propanol
Products: -
Products: -
r
2-propanol + NAD+
acetone + NADH
-
Substrates: (R)-isomer is preferred over (S)-isomer
Products: -
Products: -
r
2-propanol + NAD+
acetone + NADH
-
Substrates: (R)-isomer is preferred over (S)-isomer
Products: -
Products: -
r
3,5-bis(trifluoromethyl)acetophenone + NADH + H+
(R)-[3,5-bis(trifluoromethyl)phenyl]ethanol + NAD+
Substrates: -
Products: -
Products: -
?
3,5-bis(trifluoromethyl)acetophenone + NADH + H+
(R)-[3,5-bis(trifluoromethyl)phenyl]ethanol + NAD+
Substrates: -
Products: -
Products: -
?
4-methylpentan-2-one + NADH + H+
4-methylpentan-2-ol + NAD+
Substrates: 46% of the activity with ethyl 2-oxopropanoate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
?
4-methylpentan-2-one + NADH + H+
4-methylpentan-2-ol + NAD+
Substrates: 46% of the activity with ethyl 2-oxopropanoate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
?
acetophenone + NADH + H+
phenylethanol + NAD+
-
Substrates: 171% of the activity with beta-hydroxyacetophenone
Products: -
Products: -
?
acetophenone + NADH + H+
phenylethanol + NAD+
-
Substrates: -
Products: -
Products: -
?
cycloheptanone + NADH + H+
cycloheptanol + NAD+
Substrates: 69% of the activity with ethyl 2-oxopropanoate
Products: -
Products: -
?
cycloheptanone + NADH + H+
cycloheptanol + NAD+
Substrates: 69% of the activity with ethyl 2-oxopropanoate
Products: -
Products: -
?
ethanol + NAD+
ethanal + NADH
-
Substrates: 4% of the activity with 2-propanol
Products: -
Products: -
r
ethanol + NAD+
ethanal + NADH
-
Substrates: 4% of the activity with 2-propanol
Products: -
Products: -
r
ethyl 2-oxo-4-phenylbutanoate + NADPH + H+
ethyl (2S)-2-hydroxy-4-phenylbutanoate + NADP+
-
Substrates: -
Products: 93% conversion, 99% enantiomeric excess
Products: 93% conversion, 99% enantiomeric excess
?
ethyl 2-oxo-4-phenylbutanoate + NADPH + H+
ethyl (2S)-2-hydroxy-4-phenylbutanoate + NADP+
-
Substrates: -
Products: 93% conversion, 99% enantiomeric excess
Products: 93% conversion, 99% enantiomeric excess
?
ethyl 4-chloro-3-oxobutanoate + NADH + H+
ethyl 4-chloro-3-hydroxybutanoate + NAD+
Substrates: 129% of the activity with ethyl 2-oxopropanoate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
?
ethyl 4-chloro-3-oxobutanoate + NADH + H+
ethyl 4-chloro-3-hydroxybutanoate + NAD+
Substrates: 129% of the activity with ethyl 2-oxopropanoate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
Products: chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (3S)-4-chloro-3-hydroxybutanoate + NADP+
-
Substrates: -
Products: 73.4% conversion, 99% enantiomeric excess
Products: 73.4% conversion, 99% enantiomeric excess
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (3S)-4-chloro-3-hydroxybutanoate + NADP+
-
Substrates: -
Products: 73.4% conversion, 99% enantiomeric excess
Products: 73.4% conversion, 99% enantiomeric excess
?
ethyl 4-phenyl-2-oxobutanoate + NADH + H+
ethyl (R)-4-phenyl-2-hydroxybutanoate
Substrates: enzyme catalyzes NAD(P)H-dependent asymmetric reduction to the (R)-enantiomer
Products: product is a precursor of angiotensin-converting enzyme inhibitors such as cilazapril and benazepril
Products: product is a precursor of angiotensin-converting enzyme inhibitors such as cilazapril and benazepril
?
ethyl 4-phenyl-2-oxobutanoate + NADH + H+
ethyl (R)-4-phenyl-2-hydroxybutanoate
Substrates: enzyme catalyzes NAD(P)H-dependent asymmetric reduction to the (R)-enantiomer
Products: product is a precursor of angiotensin-converting enzyme inhibitors such as cilazapril and benazepril
Products: product is a precursor of angiotensin-converting enzyme inhibitors such as cilazapril and benazepril
?
ethyl benzoylformate + NADH + H+
ethyl (R)-mandelate + NAD+
Substrates: 270% of the activity with ethyl 2-oxopropanoate
Products: 95% conversion with 99.9% enantiomeric excess
Products: 95% conversion with 99.9% enantiomeric excess
?
ethyl benzoylformate + NADH + H+
ethyl (R)-mandelate + NAD+
Substrates: 270% of the activity with ethyl 2-oxopropanoate
Products: 95% conversion with 99.9% enantiomeric excess
Products: 95% conversion with 99.9% enantiomeric excess
?
ethyl benzoylformate + NADH + H+
ethyl (R)-mandelate + NAD+
-
Substrates: completely enantioselective reaction
Products: 95% enantiomeric excess after 6 h at 50Ā°C
Products: 95% enantiomeric excess after 6 h at 50Ā°C
r
additional information
?
-
Substrates: enzyme exhibits reductase activity towards a broad spectrum of substrates including aliphatic linear, branched, and cyclic ketones, aromatic ketones, alpha-ketoesters, and beta-ketoesters. Both alpha- and beta-ketoesters serve as better substrates than ketones, but the enzymes shows a preference for alpha-ketoesters
Products: -
Products: -
?
additional information
?
-
Substrates: enzyme exhibits reductase activity towards a broad spectrum of substrates including aliphatic linear, branched, and cyclic ketones, aromatic ketones, alpha-ketoesters, and beta-ketoesters. Both alpha- and beta-ketoesters serve as better substrates than ketones, but the enzymes shows a preference for alpha-ketoesters
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme does not obey Prelog's rule and exhibits anti-Prelog enantiopreference. Hydride transfer occurs at the si faces of carbonyl group for ethyl 4-chloro-3-oxobutanoate (COBE), which is then selectively reduced to the chiral (S)-alcohol. Aromatic ketones are reduced to (R)-enantiomers, whereas keto esters are reduced to (S)-hydroxy esters with different enantioselectivities
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme does not obey Prelog's rule and exhibits anti-Prelog enantiopreference. Hydride transfer occurs at the si faces of carbonyl group for ethyl 4-chloro-3-oxobutanoate (COBE), which is then selectively reduced to the chiral (S)-alcohol. Aromatic ketones are reduced to (R)-enantiomers, whereas keto esters are reduced to (S)-hydroxy esters with different enantioselectivities
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme catalyzes transformation of aromatic beta-amino ketones to the corresponding chiral alcohols. The purified enzyme yields pure (R)-enantiomer product with high activity and utilizes NADH as the cofactor. The enzyme shows selectivity for many aromatic beta-amino ketones/alcohols such as 2-amino-acetophenone, 2-amino-4'-hydroxyacetophenone, isoproterenol, and ephedrine. Substrate specificity, overview. No or poor activity with L-Tyr, L-Phe, Trp, ethanol, methanol, acetanilide, ethalacetoacetate, 2-phenethyl alcohol, and phenylmethanol
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme catalyzes stereoselective oxidation of (R)-secondary alcohols to corresponding ketones
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme catalyzes stereoselective oxidation of (R)-secondary alcohols to corresponding ketones
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme is coupled with formate dehydrogenase and co-immobilized on SiO2 particles, the system is capable for continuous catalytic conversion of beta-hydroxyacetophenone to optically pure (R)-phenylethanediol with in situ NADH regeneration and recycling, reusable system, method overview
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme is coupled with formate dehydrogenase and co-immobilized on SiO2 particles, the system is capable for continuous catalytic conversion of beta-hydroxyacetophenone to optically pure (R)-phenylethanediol with in situ NADH regeneration and recycling, reusable system, method overview
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme mutant I86A/C295A SADH gives high conversions and very high enantiomeric excess of the anti-Prelog R-alcohols from the tested substrates, it shows broad substrate specificity for meta-substituted, but not para-substituted, acetophenones and aryl ketones
Products: -
Products: -
?
additional information
?
-
-
Substrates: substrate specificity of ADHTt in the oxidation and the reduction reactions depends on the substrate, cf. (S)-1-phenylethanol 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)
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(R)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(R)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(R)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
?
(R)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
?
(R)-1-phenylethanol + NAD+
acetophenone + NADH + H+
Substrates: activity of mutant I886A, the wild-type enzyme is (S)-specific forming (S)-1-phenylethanol
Products: -
Products: -
r
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NAD+
-
critical role of the D37 residue in discriminating NAD(H) from NADP(H)
NADH
-
critical role of the D37 residue in discriminating NAD(H) from NADP(H)
NADPH
-
clear preference for NADPH as cofactor. The phosphate group of NADPH interacts with both the side chains and main-chain amides of Arg38 and Thr15, stabilizing this cofactor significantly better than NADH
additional information
-
the enzyme shows no activity for NADPH or NADP+
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Ca2+
EDTA
-
activates to 127% activity compared to the control activity at 1 mM and to 163% at 10 mM
K+
-
activates to 167% activity compared to the control activity at 1 mM and to 193% at 100 mM
Li+
-
activates to 127% activity compared to the control activity at 1 mM and to 178% at 100 mM
Mg2+
NH4+
Zn2+
additional information
Zn2+
-
activates to 114% activity compared to the control activity at 1 mM
additional information
the addition of Mg2+ does not affect the enzyme activity significantly
additional information
-
(R)-epinephrine dehydrogenase is not a zinc metalloenzyme
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Cu2+