1.1.1.B3: (S)-specific secondary alcohol dehydrogenase
This is an abbreviated version, for detailed information about (S)-specific secondary alcohol dehydrogenase, go to the full flat file.
Reaction
Synonyms
(S)-1-phenylethanol dehydrogenase, ADH, ADH1, ADH2, ADHTt, carbonyl reductase (NADH, specific for (S)-configuration of alcohol), CRII, More, NAD+-dependent (S)-stereospecific alcohol dehydrogenase, PED, SADH, Scr2, short-chain NAD(H)-dependent alcohol dehydrogenase, SOU1, TtADH
ECTree
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Results
in table
6
20
22
21
Substrates Products
Substrates Products on EC 1.1.1.B3 - (S)-specific secondary alcohol dehydrogenase
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REACTION DIAGRAM
(R)-2-butanol + NAD+
2-butanone + NADH + H+
Nocardia fusca AKU 2123
-
6% of the activity with (RS)-2-hexanol
-
-
r
(R)-2-hexanol + NAD+
2-hexanone + NADH + H+
Nocardia fusca AKU 2123
-
30% of the activity with (RS)-2-hexanol
-
-
r
(R)-2-pentanol + NAD+
2-pentanone + NADH + H+
Nocardia fusca AKU 2123
-
15% of the activity with (RS)-2-hexanol
-
-
r
(R)-3-butyn-2-ol + NAD+
but-3-yn-2-one + NADH + H+
Nocardia fusca AKU 2123
-
0.5% of the activity with (RS)-2-hexanol
-
-
r
(R)-3-pentyn-2-ol + NAD+
pent-3-yn-2-one + NADH + H+
Nocardia fusca AKU 2123
-
5.6% of the activity with (RS)-2-hexanol
-
-
r
(S)-1,3-butanediol + NAD+ + H+
4-hydroxy-2-butanone + NADH
-
-
enantioselective oxidation of the (S)-isomer
-
?
(S)-1-phenylethanol + NAD+
1 phenylethanone + NADH + H+
-
99% ethanoselective reaction
-
-
r
(S)-3-butyn-2-ol + NAD+
but-3-yn-2-one + NADH + H+
Nocardia fusca AKU 2123
-
6.9% of the activity with (RS)-2-hexanol
-
-
r
(S)-3-pentyn-2-ol + NAD+
pent-3-yn-2-one + NADH + H+
Nocardia fusca AKU 2123
-
33% of the activity with (RS)-2-hexanol
-
-
r
(S)-alpha-tetralol + NAD+
alpha-tetralone + NADH + H+
-
99% ethanoselective reaction
-
-
r
1-chloroacetophenone + NADH + H+
(1S)-2-chloro-1-phenylethanol + NAD+
-
-
more thasn 99% enantiomeric excess
-
?
1-hexanal + NADH + H+
hexan-1-ol + NAD+
Nocardia fusca AKU 2123
-
254% of the activity with (RS)-2-hexanol
-
-
r
1-indanone + NADH + H+
(S)-1-indanol + NAD+
-
-
99% enantiomeric excess after 6 h at 50°C
-
?
2,2,2-trifluoroacetophenone + NADH + H+
?
-
completely enantioselective reaction
-
-
r
2,3-butanedione + NADH + H+
? + NAD+
9% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
2,3-pentanedione + NADH + H+
? + NAD+
82% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
2-decanone + NADH + H+
(S)-2-decanol + NAD+
Nocardia fusca AKU 2123
-
159% of the activity with (RS)-2-hexanol
reaction is stereoselective
-
r
2-heptanone + NADH + H+
(S)-2-heptanol + NAD+
Nocardia fusca AKU 2123
-
334% of the activity with (RS)-2-hexanol
reaction is stereoselective
-
r
2-hexanone + NADH + H+
(S)-2-hexanol + NAD+
Nocardia fusca AKU 2123
-
225% of the activity with (RS)-2-hexanol
reaction is stereoselective
-
r
2-octanone + NADH + H+
(S)-2-octanol + NAD+
Nocardia fusca AKU 2123
-
223% of the activity with (RS)-2-hexanol
reaction is stereoselective
-
r
4'-chloroacetophenone + NADH + H+
(1S)-1-(4-chlorophenyl)ethanol + NAD+
-
83% of the activity with acetophenone
-
-
?
4'-fluoroacetophenone + NADH + H+
(1S)-1-(4-fluorophenyl)ethanol + NAD+
-
117% of the activity with acetophenone
-
-
?
4'-iodoacetophenone + NADH + H+
(1S)-1-(4-iodophenyl)ethanol + NAD+
-
31% of the activity with acetophenone
-
-
?
4-chloro-3-oxobutanoate + NADH + H+
(S)-4-chloro-3-hydroxybutanoate + NAD+
-
99% enantiomeric excess of (S)-enantiomer
-
?
6-methyl-5-hepten-2-one + NADH + H+
(S)-6-methyl-5-hepten-2-ol + NAD+
Nocardia fusca AKU 2123
-
-
188% of the activity with (RS)-2-hexanol
-
r
acetophenone + NADH + H+
(1S)-1-phenylethanol + NAD+
-
-
enantiomeric excess of more than 99% for (S)-configuration of product
-
?
acetophenone + NADH + H+
alpha-phenylethanol + NAD+
87% of the activity with phenylacetaldehyde
-
-
?
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+
Nocardia fusca AKU 2123
-
-
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 (S)-4-chloro-3-hydroxybutanoate + NAD+
-
product in more than 99% enantiomeric excess
-
?
methyl 4-chloro-3-oxobutanoate + NADPH + H+
methyl (S)-4-chloro-3-hydroxybutanoate + NADP+
-
-
-
?
n-valeraldehyde + NADH + H+
? + NAD+
Nocardia fusca AKU 2123
-
84% of the activity with (RS)-2-hexanol
-
-
r
p-chloro-acetophenone + NADH + H+
alpha-(p-chlorophenyl)ethanol + NAD+
288% of the activity with phenylacetaldehyde
-
-
?
phenylacetaldehyde + NADH + H+
2-phenylethanol + NAD+
-
-
-
?
pyruvic acid ethyl ester + NADH + H+
? + NAD+
Nocardia fusca AKU 2123
-
225% of the activity with (RS)-2-hexanol
-
-
r
valeraldehyde + NADH + H+
n-pentanol + NAD+
433% of the activity with phenylacetaldehyde
-
-
?
1-phenylethanone + NADH + H+
Nocardia fusca AKU 2123
-
0.9% of the activity with (RS)-2-hexanol
-
-
r
(R)-1-phenylethanol + NAD+
1-phenylethanone + NADH + H+
Nocardia fusca AKU 2123
-
21% of the activity with (RS)-2-hexanol
-
-
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+
-
asymmetric reduction of acetophenone to produce (S)-1-phenylethanol, with an enantiomeric excess of more than 99%
-
-
r
(S)-2-hexanol + NAD+
2-hexanone + NADH + H+
Nocardia fusca AKU 2123
-
reaction is stereoselective
-
-
r
(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
-
-
?
(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
-
-
?
(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
-
-
?
(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
-
?
(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
-
-
?
(S)-1-phenylethanol + NAD+
-
completely enantioselective reaction
99% enantiomeric excess after 6 h at 50°C
-
r
ethyl (R)-4-chloro-3-hydroxybutanoate + NAD+
-
-
-
-
r
ethyl 4-chloro-3-oxobutanoate + NADH + H+
ethyl (R)-4-chloro-3-hydroxybutanoate + NAD+
Nocardia fusca AKU 2123
-
-
-
-
r
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+
-
-
-
?
?
-
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
?
-
Nocardia fusca AKU 2123
-
primary alcohols are not accepted as substrate
-
-
-
additional information
?
-
-
the enzyme catalyzes stereoselective oxidation of (S)-secondary alcohols to corresponding ketones
-
-
-
additional information
?
-
Rhodotorula sp. AS2.2241
-
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)
-
-
-