HOME
login
history
all enzymes
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
1.1.1.B3 (S)-specific secondary alcohol dehydrogenaseAdvanced search results
results (
results (
Please login to have access to the AMENDA and FRENDA dataResults
in table
6
20
22
21
Substrates Products
Substrates Products on EC 1.1.1.B3 - (S)-specific secondary alcohol dehydrogenase
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
top
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(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
-
-
?
(R)-1-phenylethanol + NAD+
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-butanol + NAD+
2-butanone + NADH + H+
Nocardia fusca AKU 2123
-
27% of the activity with (RS)-2-hexanol
-
-
r
(S)-2-hexanol + NAD+
2-hexanone + NADH + H+
Nocardia fusca AKU 2123
-
121% of the activity with (RS)-2-hexanol
-
-
r
(S)-2-hexanol + NAD+
2-hexanone + NADH + H+
Nocardia fusca AKU 2123
-
reaction is stereoselective
-
-
r
(S)-2-pentanol + NAD+
2-pentanone + NADH + H+
Nocardia fusca AKU 2123
-
91% of the activity with (RS)-2-hexanol
-
-
r
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+
(S)-1-phenylethanol + NAD+
-
completely enantioselective reaction
99% enantiomeric excess after 6 h at 50°C
-
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+
Nocardia fusca AKU 2123
-
-
-
-
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+
-
-
-
?
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
?
-
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)
-
-
-
Information
