BRENDA - Enzyme Database show
show all sequences of 1.1.1.311

Asymmetric reduction of ketones and beta-keto esters by (S)-1-phenylethanol dehydrogenase from denitrifying bacterium Aromatoleum aromaticum

Dudzik, A.; Snoch, W.; Borowiecki, P.; Opalinska-Piskorz, J.; Witko, M.; Heider, J.; Szaleniec, M.; Appl. Microbiol. Biotechnol. 99, 5055-5069 (2015)

Data extracted from this reference:

Application
Application
Commentary
Organism
synthesis
application of (S)-1-phenylethanol dehydrogenase for asymmetric reduction of 42 prochiral ketones and 11 beta-keto esters to enantiopure secondary alcohols. The conversions are carried out in a batch reactor using recombinant Escherichia coli as whole-cell catalysts and isopropanol as reaction solvent and cosubstrate for NADH recovery. Ketones are converted to the respective secondary alcohols with excellent enantiomeric excesses and high productivities
Aromatoleum aromaticum
Cloned(Commentary)
Commentary
Organism
expression in Escherichia coli
Aromatoleum aromaticum
Crystallization (Commentary)
Crystallization
Organism
docking simulation for prochiral ketone and beta-keto ester substrates
Aromatoleum aromaticum
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Aromatoleum aromaticum
Q5P5I4
-
-
Aromatoleum aromaticum EbN1
Q5P5I4
-
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
2,2,2-trifluoroacetophenone + NADH + H+
-
739947
Aromatoleum aromaticum
(S)-1-phenyl-2,2,2-trifluoroethan-1-ol + NAD+
100% enantiomertic excess
-
-
?
2,2,2-trifluoroacetophenone + NADH + H+
-
739947
Aromatoleum aromaticum EbN1
(S)-1-phenyl-2,2,2-trifluoroethan-1-ol + NAD+
100% enantiomertic excess
-
-
?
2,4'-dichloroacetophenone + NADH + H+
-
739947
Aromatoleum aromaticum
(S)-2-chloro-1-(4-chloro-phenyl)-ethanol + NAD+
100% enantiomeric excess
-
-
?
2,4'-dichloroacetophenone + NADH + H+
-
739947
Aromatoleum aromaticum EbN1
(S)-2-chloro-1-(4-chloro-phenyl)-ethanol + NAD+
100% enantiomeric excess
-
-
?
4'-hydroxyacetophenone + NADH + H+
-
739947
Aromatoleum aromaticum
(S)-4-(1-hydroxyethyl)phenol + NAD+
90% enantiomeric excess
-
-
?
4-acetylbiphenyl + NADH + H+
-
739947
Aromatoleum aromaticum
(S)-1-(biphenyl-4-yl)ethanol + NAD+
100% enantiomeric excess
-
-
?
4-acetylbiphenyl + NADH + H+
-
739947
Aromatoleum aromaticum EbN1
(S)-1-(biphenyl-4-yl)ethanol + NAD+
100% enantiomeric excess
-
-
?
4-aminoacetophenone + NADH + H+
-
739947
Aromatoleum aromaticum
1-(4-aminophenyl)ethanol + NAD+
racemic product
-
-
?
4-aminoacetophenone + NADH + H+
-
739947
Aromatoleum aromaticum EbN1
1-(4-aminophenyl)ethanol + NAD+
racemic product
-
-
?
acetophenone + NADH + H+
-
739947
Aromatoleum aromaticum
(S)-1-phenylethanol + NAD+
100% enantiomeric excess
-
-
?
acetophenone + NADH + H+
-
739947
Aromatoleum aromaticum EbN1
(S)-1-phenylethanol + NAD+
100% enantiomeric excess
-
-
?
methyl 4-fluorobenzoylacetate + NADH + H+
-
739947
Aromatoleum aromaticum
(S)-methyl 3-(4-fluorophenyl)-3-hydroxypropanoate + NAD+
100% enantiomertic excess
-
-
?
Application (protein specific)
Application
Commentary
Organism
synthesis
application of (S)-1-phenylethanol dehydrogenase for asymmetric reduction of 42 prochiral ketones and 11 beta-keto esters to enantiopure secondary alcohols. The conversions are carried out in a batch reactor using recombinant Escherichia coli as whole-cell catalysts and isopropanol as reaction solvent and cosubstrate for NADH recovery. Ketones are converted to the respective secondary alcohols with excellent enantiomeric excesses and high productivities
Aromatoleum aromaticum
Cloned(Commentary) (protein specific)
Commentary
Organism
expression in Escherichia coli
Aromatoleum aromaticum
Crystallization (Commentary) (protein specific)
Crystallization
Organism
docking simulation for prochiral ketone and beta-keto ester substrates
Aromatoleum aromaticum
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
2,2,2-trifluoroacetophenone + NADH + H+
-
739947
Aromatoleum aromaticum
(S)-1-phenyl-2,2,2-trifluoroethan-1-ol + NAD+
100% enantiomertic excess
-
-
?
2,2,2-trifluoroacetophenone + NADH + H+
-
739947
Aromatoleum aromaticum EbN1
(S)-1-phenyl-2,2,2-trifluoroethan-1-ol + NAD+
100% enantiomertic excess
-
-
?
2,4'-dichloroacetophenone + NADH + H+
-
739947
Aromatoleum aromaticum
(S)-2-chloro-1-(4-chloro-phenyl)-ethanol + NAD+
100% enantiomeric excess
-
-
?
2,4'-dichloroacetophenone + NADH + H+
-
739947
Aromatoleum aromaticum EbN1
(S)-2-chloro-1-(4-chloro-phenyl)-ethanol + NAD+
100% enantiomeric excess
-
-
?
4'-hydroxyacetophenone + NADH + H+
-
739947
Aromatoleum aromaticum
(S)-4-(1-hydroxyethyl)phenol + NAD+
90% enantiomeric excess
-
-
?
4-acetylbiphenyl + NADH + H+
-
739947
Aromatoleum aromaticum
(S)-1-(biphenyl-4-yl)ethanol + NAD+
100% enantiomeric excess
-
-
?
4-acetylbiphenyl + NADH + H+
-
739947
Aromatoleum aromaticum EbN1
(S)-1-(biphenyl-4-yl)ethanol + NAD+
100% enantiomeric excess
-
-
?
4-aminoacetophenone + NADH + H+
-
739947
Aromatoleum aromaticum
1-(4-aminophenyl)ethanol + NAD+
racemic product
-
-
?
4-aminoacetophenone + NADH + H+
-
739947
Aromatoleum aromaticum EbN1
1-(4-aminophenyl)ethanol + NAD+
racemic product
-
-
?
acetophenone + NADH + H+
-
739947
Aromatoleum aromaticum
(S)-1-phenylethanol + NAD+
100% enantiomeric excess
-
-
?
acetophenone + NADH + H+
-
739947
Aromatoleum aromaticum EbN1
(S)-1-phenylethanol + NAD+
100% enantiomeric excess
-
-
?
methyl 4-fluorobenzoylacetate + NADH + H+
-
739947
Aromatoleum aromaticum
(S)-methyl 3-(4-fluorophenyl)-3-hydroxypropanoate + NAD+
100% enantiomertic excess
-
-
?
Other publictions for EC 1.1.1.311
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
739947
Dudzik
Asymmetric reduction of ketone ...
Aromatoleum aromaticum, Aromatoleum aromaticum EbN1
Appl. Microbiol. Biotechnol.
99
5055-5069
2015
-
1
1
1
-
-
-
-
-
-
-
-
-
5
-
-
-
-
-
-
-
-
12
-
-
-
-
-
-
-
-
-
-
-
-
-
1
1
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
12
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
685078
Hoeffken
Crystal structure and enzyme k ...
Azoarcus sp., Azoarcus sp. EbN1
Biochemistry
45
82-93
2006
-
-
1
1
-
-
1
-
-
-
2
-
-
4
-
-
1
-
-
-
-
-
2
1
1
-
-
-
1
-
-
-
-
-
-
-
-
1
-
1
-
-
-
1
-
-
-
-
2
-
-
-
-
1
-
-
-
-
2
1
1
-
-
-
1
-
-
-
-
-
-
-
-
-
707292
Kniemeyer
(S)-1-Phenylethanol dehydrogen ...
Azoarcus sp., Azoarcus sp. EbN1
Arch. Microbiol.
176
129-135
2001
-
-
-
-
-
-
2
4
-
-
2
2
-
11
-
-
1
-
-
1
1
-
6
1
-
-
-
4
2
-
-
2
-
1
-
-
-
-
2
-
-
-
-
2
-
4
-
-
2
2
-
-
-
1
-
1
1
-
6
1
-
-
-
4
2
-
-
1
-
-
-
-
-
-