1.1.1.B4: (R)-specific secondary alcohol dehydrogenase

This is an abbreviated version, for detailed information about (R)-specific secondary alcohol dehydrogenase, go to the full flat file.

Reaction

(R)-R-CHOH-R'
+
NAD+
=
R-CO-R'
+
NADH
+
H+

Synonyms

ADH, ADH1, ADH2, ADHTt, carbonyl reductase (NADH, specific for (S)-configuration of alcohol), CHY1186, More, SDR, short-chain NAD(H)-dependent alcohol dehydrogenase

ECTree

     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

Substrates Products

Substrates Products on EC 1.1.1.B4 - (R)-specific secondary alcohol dehydrogenase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R)-(trifluoromethyl)benzyl alcohol + NADH + H+
?
show the reaction diagram
-
93% ethanoselective reaction
-
-
r
(R)-1-phenylethanol + NAD+
acetophenone + NADH + H+
show the reaction diagram
(R)-2-butanol + NAD+
2-butanone + NADH + H+
show the reaction diagram
(R)-2-pentanol + NAD+
2-pentanone + NADH + H+
show the reaction diagram
-
-
-
-
r
1,2-butanediol + NAD+
? + NADH
show the reaction diagram
-
20% of the activity with 2-propanol
-
-
r
1,2-propanediol + NAD+
? + NADH
show the reaction diagram
-
45% of the activity with 2-propanol
-
-
r
1,3-butanediol + NAD+
? + NADH
show the reaction diagram
-
126% of the activity with 2-propanol
-
-
r
1-(2-phenylcyclopropyl)ethanone + NADH
(1R)-1-(2-phenylcyclopropyl)ethanol + NAD+
show the reaction diagram
1-butanol + NAD+
butanal + NADH
show the reaction diagram
1-chloropentane-2,4-dione + NADH
(4R)-5-chloro-4-hydroxypentan-2-one + NAD+
show the reaction diagram
1-phenoxypropan-2-one + NADH
(2R)-1-phenoxypropan-2-ol + NAD+
show the reaction diagram
1-phenylethanone + NADH
(1R)-1-phenylethanol + NAD+
show the reaction diagram
1-phenylpropane-1,2-dione + NADH
(1S)-1-hydroxy-1-phenylpropan-2-one + NAD+
show the reaction diagram
1-phenylpropane-1,2-dione + NADH
? + NAD+
show the reaction diagram
-
-
-
-
r
1-propanol + NAD+
propanal + NADH
show the reaction diagram
-
9% of the activity with 2-propanol
-
-
r
2,2,2-trifluoro-1-phenylethanone + NADH
(1R)-2,2,2-trifluoro-1-phenylethanol + NAD+
show the reaction diagram
-
-
21% of the activity with 1-phenylpropane-1,2-dione
-
r
2,2,2-trifluoro-1-phenylethanone + NADH
(1S)-2,2,2-trifluoro-1-phenylethanol + NAD+
show the reaction diagram
-
-
37% yield, 92% enantiomeric excess
-
?
2,2,2-trifluoroacetophenone + NADH + H+
(1R)-2,2,2-trifluoro-1-phenylethanol + NAD+
show the reaction diagram
-
completely enantioselective reaction
-
-
r
2,3-butanediol + NAD+
? + NADH
show the reaction diagram
2-butanol + NAD+
2-butanone + NADH
show the reaction diagram
-
(R)-isomer is preferred over (S)-isomer
-
-
r
2-butanone + NAD+
2-butanol + NADH + H+
show the reaction diagram
-
274% of the activity with beta-hydroxyacetophenone
-
-
?
2-butanone + NADH
(S)-2-hydroxybutane + NAD+
show the reaction diagram
2-butanone + NADH
2-butanol + NAD+
show the reaction diagram
-
83% of the activity with acetone
-
-
r
2-heptanone + NAD+
2-heptanol + NADH + H+
show the reaction diagram
-
281% of the activity with beta-hydroxyacetophenone
-
-
?
2-hexanone + NAD+
2-hexanol + NADH + H+
show the reaction diagram
-
259% of the activity with beta-hydroxyacetophenone
-
-
?
2-octanone + NAD+
2-octanol + NADH + H+
show the reaction diagram
-
350% of the activity with beta-hydroxyacetophenone
-
-
?
2-pentanol + NAD+
2-pentanone + NADH
show the reaction diagram
2-pentanone + NAD+
2-pentanol + NADH + H+
show the reaction diagram
-
249% of the activity with beta-hydroxyacetophenone
-
-
?
2-pentanone + NADH
(S)-2-hydroxypentane + NAD+
show the reaction diagram
-
6% of the activity with 2-butanone
-
-
r
2-pentanone + NADH
2-pentanol + NAD+
show the reaction diagram
-
44% of the activity with acetone
-
-
r
2-propanol + NAD+
acetone + NADH
show the reaction diagram
2-propanol + NAD+ + H+
acetone + NADH
show the reaction diagram
-
-
-
-
r
3-(dimethylamino)-1-phenylpropan-1-one + NADH
(1S)-3-dimethylamino-1-phenylpropan-1-ol + NAD+
show the reaction diagram
-
-
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+
show the reaction diagram
-
336% of the activity with 2-butanone
-
-
r
3-hexanone + NAD+
3-hexanol + NADH + H+
show the reaction diagram
-
29% of the activity with beta-hydroxyacetophenone
-
-
?
3-pentanol + NAD+
3-pentanone + NADH
show the reaction diagram
-
23% of the activity with 2-propanol
-
-
r
3-pentanone + NAD+
3-pentanol + NADH + H+
show the reaction diagram
-
35% of the activity with beta-hydroxyacetophenone
-
-
?
3-pentanone + NADH
3-pentanol + NAD+
show the reaction diagram
-
16% of the activity with acetone
-
-
r
4-hydroxy-2-butanone + NADH
? + NAD+
show the reaction diagram
-
95% of the activity with acetone
-
-
r
4-methylpentan-2-one + NADH + H+
4-methylpentan-2-ol + NAD+
show the reaction diagram
4-phenylbutan-2-one + NADH
(2R)-4-phenylbutan-2-ol + NAD+
show the reaction diagram
-
-
18% of the activity with 1-phenylpropane-1,2-dione
-
r
5-chloropentan-2-one + NADH
(2S)-5-chloropentan-2-ol + NAD+
show the reaction diagram
-
-
48% yield, 93% enantiomeric excess
-
?
6-methylhept-5-en-2-one + NADH
(2S)-6-methylhept-5-en-2-ol + NAD+
show the reaction diagram
-
-
51% yield, 97% enantiomeric excess
-
?
acetone + NAD+
isopropanol + NADH + H+
show the reaction diagram
-
260% of the activity with beta-hydroxyacetophenone
-
-
?
acetone + NADH
2-propanol + NAD+
show the reaction diagram
-
-
-
-
r
acetophenone + NADH + H+
phenylethanol + NAD+
show the reaction diagram
acetophenone + NADPH + H+
phenylethanol + NADP+
show the reaction diagram
-
-
-
-
?
beta-hydroxyacetophenone + NAD+
(R)-1-phenyl-1,2-ethanediol + NADH + H+
show the reaction diagram
-
-
formation of (R)-enantiomner with 100% enantiomeric excess
-
?
cycloheptanone + NADH + H+
cycloheptanol + NAD+
show the reaction diagram
ethanol + NAD+
ethanal + NADH
show the reaction diagram
ethyl (R)-mandelate + NADH + H+
ethyl benzoylformate + NAD+
show the reaction diagram
-
95% ethanoselective reaction
-
-
r
ethyl 2-oxo-3-phenylpropanoate + NADH + H+
ethyl 2-hydroxy-3-phenylpropanoate + NAD+
show the reaction diagram
ethyl 2-oxo-4-phenylbutanoate + NADH + H+
ethyl 2-hydroxy-4-phenylbutanoate + NAD+
show the reaction diagram
135% of the activity with ethyl 2-oxopropanoate
chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
-
?
ethyl 2-oxopropanoate + NADH + H+
ethyl 2-hydroxypropanoate + NAD+
show the reaction diagram
-
chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
-
?
ethyl 3-oxohexanoate + NADH + H+
ethyl 3-hydroxyhexanoate + NAD+
show the reaction diagram
105% of the activity with ethyl 2-oxopropanoate
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+
show the reaction diagram
ethyl benzoylformate + NADH + H+
ethyl (R)-mandelate + NAD+
show the reaction diagram
-
completely enantioselective reaction
95% enantiomeric excess after 6 h at 50°C
-
r
ethyl benzoylformate + NADH + H+
ethyl (R)-mandelate+ NAD+
show the reaction diagram
270% of the activity with ethyl 2-oxopropanoate
95% conversion with 99.9% enantiomeric excess
-
?
ethyl oxo(phenyl)acetate + NADH + H+
ethyl hydroxy(phenyl)acetate + NAD+
show the reaction diagram
270% of the activity with ethyl 2-oxopropanoate
chirality of the product not determined. The enzyme prouces ethyl (R)-mandelate from ethal benzoylformate
-
?
hydroxyacetone + NADH
? + NAD+
show the reaction diagram
-
92% of the activity with acetone
-
-
r
methyl (R)-mandelate + NADH + H+
methyl benzoylformate + NAD+
show the reaction diagram
-
92% ethanoselective reaction
-
-
r
methyl 3-oxobutanoate + NADH
methyl (3S)-3-hydroxybutanoate + NAD+
show the reaction diagram
-
135% of the activity with 2-butanone
-
-
r
methyl benzoylformate + NADH + H+
methyl (R)-mandelate + NAD+
show the reaction diagram
-
completely enantioselective reaction
92% enantiomeric excess after 6 h at 50°C
-
r
methyl oxo(phenyl)acetate + NADH
methyl (2S)-hydroxy(phenyl)ethanoate + NAD+
show the reaction diagram
-
-
79% yield, 98% enantiomeric excess
-
?
methylpyruvate + NADH
? + NAD+
show the reaction diagram
-
64% of the activity with acetone
-
-
r
pentane-2,4-dione + NADH
(4R)-4-hydroxypentan-2-one + NAD+
show the reaction diagram
-
32% of the activity with 2-butanone
-
-
r
additional information
?
-