BRENDA - Enzyme Database show
show all sequences of 1.1.1.B4

A Pseudomonas sp. alcohol dehydrogenase with broad substrate specificity and unusual stereospecificity for organic synthesis

Bradshaw, C.W.; Fu, H.; Shen, G.-J.; Wong, C.-H; J. Org. Chem. 57, 1526-1532 (1992)
No PubMed abstract available

Data extracted from this reference:

KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.075
-
2-propanol
-
Pseudomonas sp.
0.525
-
NAD+
-
Pseudomonas sp.
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Pseudomonas sp.
-
strain PED, growth on 1-phenyl-1,2-ethanediol as sole carbon source
-
Pseudomonas sp. PED
-
strain PED, growth on 1-phenyl-1,2-ethanediol as sole carbon source
-
Reaction
Reaction
Commentary
Organism
(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
Pseudomonas sp.
Specific Activity [micromol/min/mg]
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
36
-
pH 8.5, 30°C, substrate 2-propanol
Pseudomonas sp.
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1-(2-phenylcyclopropyl)ethanone + NADH
-
688571
Pseudomonas sp.
(1R)-1-(2-phenylcyclopropyl)ethanol + NAD+
18% of the activity with 1-phenylpropane-1,2-dione
-
-
r
1-(2-phenylcyclopropyl)ethanone + NADH
-
688571
Pseudomonas sp. PED
(1R)-1-(2-phenylcyclopropyl)ethanol + NAD+
18% of the activity with 1-phenylpropane-1,2-dione
-
-
r
1-chloropentane-2,4-dione + NADH
-
688571
Pseudomonas sp.
(4R)-5-chloro-4-hydroxypentan-2-one + NAD+
76% yield, 98% enantiomeric excess
-
-
?
1-chloropentane-2,4-dione + NADH
-
688571
Pseudomonas sp. PED
(4R)-5-chloro-4-hydroxypentan-2-one + NAD+
76% yield, 98% enantiomeric excess
-
-
?
1-phenoxypropan-2-one + NADH
-
688571
Pseudomonas sp.
(2R)-1-phenoxypropan-2-ol + NAD+
21% of the activity with 1-phenylpropane-1,2-dione
-
-
r
1-phenoxypropan-2-one + NADH
-
688571
Pseudomonas sp. PED
(2R)-1-phenoxypropan-2-ol + NAD+
21% of the activity with 1-phenylpropane-1,2-dione
-
-
r
1-phenylethanone + NADH
-
688571
Pseudomonas sp.
(1R)-1-phenylethanol + NAD+
34% yield, 94% enantiomeric excess
-
-
?
1-phenylethanone + NADH
-
688571
Pseudomonas sp. PED
(1R)-1-phenylethanol + NAD+
34% yield, 94% enantiomeric excess
-
-
?
1-phenylpropane-1,2-dione + NADH
-
688571
Pseudomonas sp.
(1S)-1-hydroxy-1-phenylpropan-2-one + NAD+
83% yield, 86% enantiomeric excess
-
-
?
1-phenylpropane-1,2-dione + NADH
-
688571
Pseudomonas sp. PED
(1S)-1-hydroxy-1-phenylpropan-2-one + NAD+
83% yield, 86% enantiomeric excess
-
-
?
1-phenylpropane-1,2-dione + NADH
-
688571
Pseudomonas sp.
? + NAD+
-
-
-
r
2,2,2-trifluoro-1-phenylethanone + NADH
-
688571
Pseudomonas sp.
(1R)-2,2,2-trifluoro-1-phenylethanol + NAD+
21% of the activity with 1-phenylpropane-1,2-dione
-
-
r
2,2,2-trifluoro-1-phenylethanone + NADH
-
688571
Pseudomonas sp.
(1S)-2,2,2-trifluoro-1-phenylethanol + NAD+
37% yield, 92% enantiomeric excess
-
-
?
2-butanone + NADH
-
688571
Pseudomonas sp.
(S)-2-hydroxybutane + NAD+
-
-
-
r
2-pentanone + NADH
6% of the activity with 2-butanone
688571
Pseudomonas sp.
(S)-2-hydroxypentane + NAD+
-
-
-
r
2-propanol + NAD+ + H+
-
688571
Pseudomonas sp.
acetone + NADH
-
-
-
r
3-(dimethylamino)-1-phenylpropan-1-one + NADH
-
688571
Pseudomonas sp.
(1S)-3-dimethylamino-1-phenylpropan-1-ol + NAD+
24% of the activity with 1-phenylpropane-1,2-dione
-
-
r
3-chloro-pentane-2,4-dione + NADH
336% of the activity with 2-butanone
688571
Pseudomonas sp.
(4R)-3-chloro-4-hydroxypentan-2-one + NAD+
-
-
-
r
4-phenylbutan-2-one + NADH
-
688571
Pseudomonas sp.
(2R)-4-phenylbutan-2-ol + NAD+
18% of the activity with 1-phenylpropane-1,2-dione
-
-
r
5-chloropentan-2-one + NADH
-
688571
Pseudomonas sp.
(2S)-5-chloropentan-2-ol + NAD+
48% yield, 93% enantiomeric excess
-
-
?
6-methylhept-5-en-2-one + NADH
-
688571
Pseudomonas sp.
(2S)-6-methylhept-5-en-2-ol + NAD+
51% yield, 97% enantiomeric excess
-
-
?
methyl 3-oxobutanoate + NADH
135% of the activity with 2-butanone
688571
Pseudomonas sp.
methyl (3S)-3-hydroxybutanoate + NAD+
-
-
-
r
methyl oxo(phenyl)acetate + NADH
-
688571
Pseudomonas sp.
methyl (2S)-hydroxy(phenyl)ethanoate + NAD+
79% yield, 98% enantiomeric excess
-
-
?
pentane-2,4-dione + NADH
32% of the activity with 2-butanone
688571
Pseudomonas sp.
(4R)-4-hydroxypentan-2-one + NAD+
-
-
-
r
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.1
-
reduction
Pseudomonas sp.
8.5
-
oxidation
Pseudomonas sp.
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.075
-
2-propanol
-
Pseudomonas sp.
0.525
-
NAD+
-
Pseudomonas sp.
Specific Activity [micromol/min/mg] (protein specific)
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
36
-
pH 8.5, 30°C, substrate 2-propanol
Pseudomonas sp.
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1-(2-phenylcyclopropyl)ethanone + NADH
-
688571
Pseudomonas sp.
(1R)-1-(2-phenylcyclopropyl)ethanol + NAD+
18% of the activity with 1-phenylpropane-1,2-dione
-
-
r
1-(2-phenylcyclopropyl)ethanone + NADH
-
688571
Pseudomonas sp. PED
(1R)-1-(2-phenylcyclopropyl)ethanol + NAD+
18% of the activity with 1-phenylpropane-1,2-dione
-
-
r
1-chloropentane-2,4-dione + NADH
-
688571
Pseudomonas sp.
(4R)-5-chloro-4-hydroxypentan-2-one + NAD+
76% yield, 98% enantiomeric excess
-
-
?
1-chloropentane-2,4-dione + NADH
-
688571
Pseudomonas sp. PED
(4R)-5-chloro-4-hydroxypentan-2-one + NAD+
76% yield, 98% enantiomeric excess
-
-
?
1-phenoxypropan-2-one + NADH
-
688571
Pseudomonas sp.
(2R)-1-phenoxypropan-2-ol + NAD+
21% of the activity with 1-phenylpropane-1,2-dione
-
-
r
1-phenoxypropan-2-one + NADH
-
688571
Pseudomonas sp. PED
(2R)-1-phenoxypropan-2-ol + NAD+
21% of the activity with 1-phenylpropane-1,2-dione
-
-
r
1-phenylethanone + NADH
-
688571
Pseudomonas sp.
(1R)-1-phenylethanol + NAD+
34% yield, 94% enantiomeric excess
-
-
?
1-phenylethanone + NADH
-
688571
Pseudomonas sp. PED
(1R)-1-phenylethanol + NAD+
34% yield, 94% enantiomeric excess
-
-
?
1-phenylpropane-1,2-dione + NADH
-
688571
Pseudomonas sp.
(1S)-1-hydroxy-1-phenylpropan-2-one + NAD+
83% yield, 86% enantiomeric excess
-
-
?
1-phenylpropane-1,2-dione + NADH
-
688571
Pseudomonas sp. PED
(1S)-1-hydroxy-1-phenylpropan-2-one + NAD+
83% yield, 86% enantiomeric excess
-
-
?
1-phenylpropane-1,2-dione + NADH
-
688571
Pseudomonas sp.
? + NAD+
-
-
-
r
2,2,2-trifluoro-1-phenylethanone + NADH
-
688571
Pseudomonas sp.
(1R)-2,2,2-trifluoro-1-phenylethanol + NAD+
21% of the activity with 1-phenylpropane-1,2-dione
-
-
r
2,2,2-trifluoro-1-phenylethanone + NADH
-
688571
Pseudomonas sp.
(1S)-2,2,2-trifluoro-1-phenylethanol + NAD+
37% yield, 92% enantiomeric excess
-
-
?
2-butanone + NADH
-
688571
Pseudomonas sp.
(S)-2-hydroxybutane + NAD+
-
-
-
r
2-pentanone + NADH
6% of the activity with 2-butanone
688571
Pseudomonas sp.
(S)-2-hydroxypentane + NAD+
-
-
-
r
2-propanol + NAD+ + H+
-
688571
Pseudomonas sp.
acetone + NADH
-
-
-
r
3-(dimethylamino)-1-phenylpropan-1-one + NADH
-
688571
Pseudomonas sp.
(1S)-3-dimethylamino-1-phenylpropan-1-ol + NAD+
24% of the activity with 1-phenylpropane-1,2-dione
-
-
r
3-chloro-pentane-2,4-dione + NADH
336% of the activity with 2-butanone
688571
Pseudomonas sp.
(4R)-3-chloro-4-hydroxypentan-2-one + NAD+
-
-
-
r
4-phenylbutan-2-one + NADH
-
688571
Pseudomonas sp.
(2R)-4-phenylbutan-2-ol + NAD+
18% of the activity with 1-phenylpropane-1,2-dione
-
-
r
5-chloropentan-2-one + NADH
-
688571
Pseudomonas sp.
(2S)-5-chloropentan-2-ol + NAD+
48% yield, 93% enantiomeric excess
-
-
?
6-methylhept-5-en-2-one + NADH
-
688571
Pseudomonas sp.
(2S)-6-methylhept-5-en-2-ol + NAD+
51% yield, 97% enantiomeric excess
-
-
?
methyl 3-oxobutanoate + NADH
135% of the activity with 2-butanone
688571
Pseudomonas sp.
methyl (3S)-3-hydroxybutanoate + NAD+
-
-
-
r
methyl oxo(phenyl)acetate + NADH
-
688571
Pseudomonas sp.
methyl (2S)-hydroxy(phenyl)ethanoate + NAD+
79% yield, 98% enantiomeric excess
-
-
?
pentane-2,4-dione + NADH
32% of the activity with 2-butanone
688571
Pseudomonas sp.
(4R)-4-hydroxypentan-2-one + NAD+
-
-
-
r
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.1
-
reduction
Pseudomonas sp.
8.5
-
oxidation
Pseudomonas sp.
Other publictions for EC 1.1.1.B4
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)
721911
Zhou
Biocatalytic characterization ...
Carboxydothermus hydrogenoformans, Carboxydothermus hydrogenoformans DSM 6008
Biotechnol. Lett.
35
359-365
2013
-
1
1
-
-
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-
1
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-
1
-
4
2
-
-
-
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15
1
1
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1
1
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2
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1
1
2
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1
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1
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4
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15
1
1
-
-
1
1
-
-
-
-
-
-
-
-
-
723841
Protsko
Crystallization and preliminar ...
Thermoanaerobacter ethanolicus
Acta Crystallogr. Sect. F
66
831-833
2010
-
-
1
1
1
-
-
-
-
-
1
1
-
1
-
-
1
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1
1
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2
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1
2
1
1
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1
1
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1
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1
1
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1
1
-
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-
725726
Li
-
Deracemization of aryl seconda ...
Microbacterium oxydans, Microbacterium oxydans ECU2010
J. Mol. Catal. B
64
48-52
2010
-
1
-
-
-
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2
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2
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4
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2
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2
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4
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697267
Pal
Activity of yeast alcohol dehy ...
Saccharomyces carlsbergensis, Saccharomyces carlsbergensis Y379-50, Saccharomyces cerevisiae
Chem. Biol. Interact.
178
16-23
2009
-
-
-
-
-
-
-
-
1
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3
-
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3
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2
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2
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1
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3
-
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-
-
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-
-
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-
-
697839
Pennacchio
Role of Tryptophan 95 in subst ...
Sulfolobus solfataricus
Extremophiles
13
751-761
2009
-
-
1
1
1
-
-
4
-
-
-
-
-
1
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1
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2
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4
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1
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1
1
1
1
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4
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1
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2
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4
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-
-
-
-
-
-
-
-
-
711860
Machielsen
-
Cofactor engineering of Lactob ...
Lactobacillus brevis
Eng. Life Sci.
9
38-44
2009
-
-
1
-
5
-
-
4
-
-
-
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1
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2
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2
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2
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1
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1
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5
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2
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2
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2
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4
4
684583
Pennacchio
Purification and characterizat ...
Thermus thermophilus
Appl. Environ. Microbiol.
74
3949-3958
2008
1
1
1
-
-
-
7
5
-
5
4
-
1
1
-
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1
-
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7
1
2
1
4
4
2
2
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3
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1
1
1
3
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7
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5
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5
4
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1
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1
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7
1
2
1
4
4
2
2
-
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-
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688747
Nie
A novel NADH-dependent carbony ...
Candida parapsilosis
Lett. Appl. Microbiol.
44
555-562
2007
-
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9
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1
1
2
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1
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1
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1
10
1
1
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1
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2
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9
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1
1
2
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1
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1
1
10
1
1
-
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1
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687864
Isobe
Thermostable NAD+-dependent (R ...
Burkholderia sp., Burkholderia sp. AIU 652
J. Biosci. Bioeng.
96
387-393
2003
-
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6
15
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2
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3
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1
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1
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24
1
1
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1
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3
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3
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1
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-
3
-
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-
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6
-
15
-
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2
-
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1
-
-
1
-
24
1
1
-
1
-
3
-
-
1
-
-
-
-
-
-
688571
Bradshaw
-
A Pseudomonas sp. alcohol dehy ...
Pseudomonas sp., Pseudomonas sp. PED
J. Org. Chem.
57
1526-1532
1992
-
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2
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2
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1
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1
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24
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2
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2
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1
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24
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2
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