BRENDA - Enzyme Database show
show all sequences of 1.1.1.159

Enzymatic enantioselective reduction of alpha-ketoesters by a thermostable 7alpha-hydroxysteroid dehydrogenase from Bacteroides fragilis

Zhu, D.; Stearns, J.E.; Ramirez, M.; Hua, L.; Tetrahedron 62, 4535-4539 (2006)
No PubMed abstract available

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
overexpression in Escherichia coli
Bacteroides fragilis
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
7-keto-lithocholic acid + NADH
Bacteroides fragilis
in the gastrointestinal tract of host organisms
cheno-deoxycholic acid + NAD+
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Bacteroides fragilis
-
strain ATCC 25285
-
Purification (Commentary)
Commentary
Organism
recombinant enzyme from Escherichia coli by heat treatment at 55-60C, polyethyleneimine treatment, ammonium sulfate fractionation, and gel filtration, followed by lyophilization
Bacteroides fragilis
Specific Activity [micromol/min/mg]
Specific Activity Minimum [mol/min/mg]
Specific Activity Maximum [mol/min/mg]
Commentary
Organism
0.32
-
purified recombinant enzyme, substrate methyl benzoylformate
Bacteroides fragilis
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
7-keto-lithocholic acid + NADH
-
670926
Bacteroides fragilis
cheno-deoxycholic acid + NAD+
-
-
-
?
7-keto-lithocholic acid + NADH
in the gastrointestinal tract of host organisms
670926
Bacteroides fragilis
cheno-deoxycholic acid + NAD+
-
-
-
?
ethyl (R)-2-hydroxy-2-(3,5-difluorophenyl)acetate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-2-(3,5-difluorophenyl)acetate + NADH
-
-
-
?
ethyl (R)-2-hydroxy-3,3-dimethylbutyrate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-3,3-dimethylbutyrate + NADH
-
-
-
?
ethyl (R)-2-hydroxy-3-methylbutyrate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-3-methylbutyrate + NADH
-
-
-
?
ethyl 2-hydroxy-2-(3,4-dichlorophenyl)acetate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-2-(3,4-dichlorophenyl)acetate + NADH
-
-
-
?
ethyl 2-hydroxy-2-(4-bromophenyl)acetate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-2-(4-bromophenyl)acetate + NADH
-
-
-
?
ethyl 2-hydroxy-2-(4-chlorophenyl)acetate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-2-(4-chlorophenyl)acetate + NADH
-
-
-
?
ethyl 2-hydroxy-2-(4-cyanophenyl)acetate + NAD+
high activity
670926
Bacteroides fragilis
ethyl 2-oxo-2-(4-cyanophenyl)acetate + NADH
-
-
-
?
ethyl 2-hydroxy-2-(4-fluorophenyl)acetate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-2-(4-fluorophenyl)acetate + NADH
-
-
-
?
ethyl 2-hydroxy-2-(4-methylphenyl)acetate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-2-(4-methylphenyl)acetate + NADH
-
-
-
?
ethyl 2-hydroxy-2-cyclohexylacetate + NAD+
best substrate
670926
Bacteroides fragilis
ethyl 2-oxo-2-cyclohexylacetate + NADH
-
-
-
?
ethyl 2-hydroxy-2-phenylacetate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-2-phenylacetate + NADH
-
-
-
?
methyl 2-hydroxy-2-phenylacetate + NAD+
-
670926
Bacteroides fragilis
methyl 2-oxo-2-phenylacetate + NADH
-
-
-
?
methyl benzoylformate + NADH
-
670926
Bacteroides fragilis
?
-
-
-
?
additional information
substrate specificity and stereoselectivity towards various ketones, product determination, overview
670926
Bacteroides fragilis
?
-
-
-
-
Temperature Optimum [C]
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
22
-
assay at room temperature
Bacteroides fragilis
Temperature Stability [C]
Temperature Stability Minimum [C]
Temperature Stability Maximum [C]
Commentary
Organism
additional information
-
the enzyme is thermostable
Bacteroides fragilis
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7
-
assay at
Bacteroides fragilis
Cofactor
Cofactor
Commentary
Organism
Structure
NADH
-
Bacteroides fragilis
Cloned(Commentary) (protein specific)
Commentary
Organism
overexpression in Escherichia coli
Bacteroides fragilis
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADH
-
Bacteroides fragilis
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
7-keto-lithocholic acid + NADH
Bacteroides fragilis
in the gastrointestinal tract of host organisms
cheno-deoxycholic acid + NAD+
-
-
?
Purification (Commentary) (protein specific)
Commentary
Organism
recombinant enzyme from Escherichia coli by heat treatment at 55-60C, polyethyleneimine treatment, ammonium sulfate fractionation, and gel filtration, followed by lyophilization
Bacteroides fragilis
Specific Activity [micromol/min/mg] (protein specific)
Specific Activity Minimum [mol/min/mg]
Specific Activity Maximum [mol/min/mg]
Commentary
Organism
0.32
-
purified recombinant enzyme, substrate methyl benzoylformate
Bacteroides fragilis
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
7-keto-lithocholic acid + NADH
-
670926
Bacteroides fragilis
cheno-deoxycholic acid + NAD+
-
-
-
?
7-keto-lithocholic acid + NADH
in the gastrointestinal tract of host organisms
670926
Bacteroides fragilis
cheno-deoxycholic acid + NAD+
-
-
-
?
ethyl (R)-2-hydroxy-2-(3,5-difluorophenyl)acetate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-2-(3,5-difluorophenyl)acetate + NADH
-
-
-
?
ethyl (R)-2-hydroxy-3,3-dimethylbutyrate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-3,3-dimethylbutyrate + NADH
-
-
-
?
ethyl (R)-2-hydroxy-3-methylbutyrate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-3-methylbutyrate + NADH
-
-
-
?
ethyl 2-hydroxy-2-(3,4-dichlorophenyl)acetate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-2-(3,4-dichlorophenyl)acetate + NADH
-
-
-
?
ethyl 2-hydroxy-2-(4-bromophenyl)acetate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-2-(4-bromophenyl)acetate + NADH
-
-
-
?
ethyl 2-hydroxy-2-(4-chlorophenyl)acetate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-2-(4-chlorophenyl)acetate + NADH
-
-
-
?
ethyl 2-hydroxy-2-(4-cyanophenyl)acetate + NAD+
high activity
670926
Bacteroides fragilis
ethyl 2-oxo-2-(4-cyanophenyl)acetate + NADH
-
-
-
?
ethyl 2-hydroxy-2-(4-fluorophenyl)acetate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-2-(4-fluorophenyl)acetate + NADH
-
-
-
?
ethyl 2-hydroxy-2-(4-methylphenyl)acetate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-2-(4-methylphenyl)acetate + NADH
-
-
-
?
ethyl 2-hydroxy-2-cyclohexylacetate + NAD+
best substrate
670926
Bacteroides fragilis
ethyl 2-oxo-2-cyclohexylacetate + NADH
-
-
-
?
ethyl 2-hydroxy-2-phenylacetate + NAD+
-
670926
Bacteroides fragilis
ethyl 2-oxo-2-phenylacetate + NADH
-
-
-
?
methyl 2-hydroxy-2-phenylacetate + NAD+
-
670926
Bacteroides fragilis
methyl 2-oxo-2-phenylacetate + NADH
-
-
-
?
methyl benzoylformate + NADH
-
670926
Bacteroides fragilis
?
-
-
-
?
additional information
substrate specificity and stereoselectivity towards various ketones, product determination, overview
670926
Bacteroides fragilis
?
-
-
-
-
Temperature Optimum [C] (protein specific)
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
22
-
assay at room temperature
Bacteroides fragilis
Temperature Stability [C] (protein specific)
Temperature Stability Minimum [C]
Temperature Stability Maximum [C]
Commentary
Organism
additional information
-
the enzyme is thermostable
Bacteroides fragilis
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7
-
assay at
Bacteroides fragilis
Other publictions for EC 1.1.1.159
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)
697994
Fukiya
Conversion of cholic acid and ...
Bacteroides fragilis, Bacteroides fragilis NCTC 9343, Bacteroides intestinalis, Bacteroides intestinalis am-1, Escherichia coli HB101
FEMS Microbiol. Lett.
293
263-270
2009
6
-
-
-
-
-
-
-
-
-
-
-
-
13
-
-
-
-
-
-
-
-
10
-
-
-
-
-
-
-
-
-
-
-
-
6
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
10
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
701240
Giovannini
7alpha- and 12alpha-Hydroxyste ...
Acinetobacter lwoffii
Steroids
73
1385-1390
2008
1
1
-
-
-
-
-
-
-
-
-
-
-
2
-
-
1
-
-
-
2
1
1
-
-
-
-
-
-
-
-
-
-
-
-
1
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
2
1
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
670898
Pedrini
Xanthomonas maltophilia CBS 89 ...
Stenotrophomonas maltophilia, Stenotrophomonas maltophilia CBS 897.97
Steroids
71
189-198
2006
-
1
-
-
-
-
-
2
-
-
-
1
-
3
-
-
1
-
-
-
2
1
7
-
1
-
-
-
1
-
-
2
-
-
-
-
1
-
2
-
-
-
-
-
-
2
-
-
-
1
-
-
-
1
-
-
2
1
7
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
670926
Zhu
-
Enzymatic enantioselective red ...
Bacteroides fragilis
Tetrahedron
62
4535-4539
2006
-
-
1
-
-
-
-
-
-
-
-
1
-
1
-
-
1
-
-
-
1
-
16
-
1
-
1
-
1
-
-
1
-
-
-
-
-
1
1
-
-
-
-
-
-
-
-
-
-
1
-
-
-
1
-
-
1
-
16
-
1
-
1
-
1
-
-
-
-
-
-
-
-
-
656301
Ueda
-
Molecular and enzymatic proper ...
Pseudomonas sp., Pseudomonas sp. B-0831
J. Biol. Macromol.
4
33-38
2004
-
-
-
-
-
-
-
1
-
-
2
-
-
6
-
-
1
-
-
-
-
-
6
1
-
-
-
-
-
-
-
2
-
-
-
-
-
-
2
-
-
-
-
-
-
1
-
-
2
-
-
-
-
1
-
-
-
-
6
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
655302
Bennett
Cloning and characterization o ...
Bacteroides fragilis, Clostridium scindens, Escherichia coli, Paeniclostridium sordellii
Curr. Microbiol.
47
475-484
2003
-
-
1
-
-
-
2
4
-
-
2
-
-
6
-
-
1
-
-
-
1
-
8
1
-
-
4
-
2
1
-
5
-
-
-
-
-
1
5
-
-
-
-
2
-
4
-
-
2
-
-
-
-
1
-
-
1
-
8
1
-
-
4
-
2
1
-
-
-
-
-
-
-
-
286083
Tanabe
Roles of the Ser146, Tyr159, a ...
Escherichia coli
J. Biochem.
124
634-641
1998
-
-
1
1
6
-
-
12
-
-
2
-
-
2
-
-
1
1
-
-
-
-
-
1
-
-
-
6
1
1
-
1
-
-
-
-
-
1
1
1
6
-
-
-
-
12
-
-
2
-
-
-
-
1
-
-
-
-
-
1
-
-
-
6
1
1
-
-
-
-
-
-
-
-
286081
Tanaka
Crystal structures of the bina ...
Escherichia coli
Biochemistry
35
7715-7730
1996
-
-
-
1
-
-
-
-
-
-
-
1
-
2
-
-
1
1
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
1
1
-
-
-
-
-
-
-
-
-
1
-
-
-
1
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
286084
Coleman
Characterization and regulatio ...
Paeniclostridium sordellii
J. Bacteriol.
176
4865-4874
1994
-
-
1
-
-
-
-
-
-
-
1
1
-
1
-
-
1
1
-
-
1
-
2
1
-
-
-
-
-
-
-
2
-
-
-
-
-
1
2
-
-
-
-
-
-
-
-
-
1
1
-
-
-
1
-
-
1
-
2
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
286082
Baron
Cloning, sequencing, and expre ...
Eubacterium sp., Eubacterium sp. VPI 12708
J. Bacteriol.
173
4558-4569
1991
-
-
1
-
-
-
-
-
-
-
1
4
-
12
-
-
1
-
-
-
2
-
8
1
-
-
-
-
-
-
-
2
-
-
-
-
-
1
2
-
-
-
-
-
-
-
-
-
1
4
-
-
-
1
-
-
2
-
8
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
286085
Yoshimoto
Cloning and sequencing of the ...
Escherichia coli
J. Bacteriol.
173
2173-2179
1991
-
-
1
1
-
-
12
5
-
-
2
-
-
3
-
-
1
-
-
-
-
-
6
1
-
-
-
5
1
-
1
1
-
-
-
-
-
1
1
1
-
-
-
12
-
5
-
-
2
-
-
-
-
1
-
-
-
-
6
1
-
-
-
5
1
-
1
-
-
-
-
-
-
-
286072
Prabha
Purification of 7alpha-hydroxy ...
Escherichia coli
Can. J. Microbiol.
36
131-135
1990
-
-
-
-
-
-
-
-
-
-
1
-
-
2
-
-
1
-
-
-
1
-
-
-
-
-
2
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
1
-
-
1
-
-
-
-
-
2
-
1
-
-
-
-
-
-
-
-
-
286073
Prabha
Kinetic properties of 7alpha-h ...
Escherichia coli
Can. J. Microbiol.
35
1076-1080
1989
2
-
-
-
-
-
18
-
-
4
-
-
-
1
-
-
-
-
-
-
8
-
6
-
-
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
18
-
-
-
4
-
-
-
-
-
-
-
-
8
-
6
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
286074
Ottolina
Enzymatic synthesis of [4R-2H] ...
Escherichia coli
Biochim. Biophys. Acta
998
173-178
1989
-
1
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
1
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
286075
Kinoshita
-
Purification and properties of ...
Brevibacterium fuscum
J. Ferment. Technol.
66
145-152
1988
-
-
-
-
-
-
-
8
-
-
2
-
-
1
-
-
1
-
-
-
4
-
8
1
1
1
2
-
3
-
2
1
-
-
-
-
-
-
1
-
-
-
-
-
-
8
-
-
2
-
-
-
-
1
-
-
4
-
8
1
1
1
2
-
3
-
2
-
-
-
-
-
-
-
286076
MacDonald
Bile induction of 7alpha- and ...
Clostridium sardiniense
Biochim. Biophys. Acta
665
262-269
1981
-
-
-
-
-
-
-
3
-
-
-
1
-
1
-
-
-
-
-
-
1
-
1
-
-
-
-
-
1
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
3
-
-
-
1
-
-
-
-
-
-
1
-
1
-
-
-
-
-
1
1
-
-
-
-
-
-
-
-
286077
Haslewood
The specificity of a 7alpha-hy ...
Escherichia coli
Biochem. J.
157
207-210
1976
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
7
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
7
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
286078
Hylemon
Multiple forms of 7-alpha-hydr ...
Bacteroides fragilis
J. Bacteriol.
122
418-424
1975
-
-
-
-
-
-
2
-
-
2
2
1
-
1
-
-
1
-
-
-
-
-
7
-
-
-
2
-
1
-
-
2
-
-
-
-
-
-
2
-
-
-
-
2
-
-
-
2
2
1
-
-
-
1
-
-
-
-
7
-
-
-
2
-
1
-
-
-
-
-
-
-
-
-
286079
MacDonald
NAD- and NADP-dependent 7alpha ...
Bacteroides fragilis
Biochim. Biophys. Acta
384
12-24
1975
-
-
-
-
-
1
-
7
-
-
-
-
-
3
-
-
-
-
-
-
-
-
5
-
-
-
-
-
2
-
-
2
-
-
-
-
-
-
2
-
-
1
-
-
-
7
-
-
-
-
-
-
-
-
-
-
-
-
5
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
286080
MacDonald
7alpha-hydroxysteroid dehydrog ...
Escherichia coli
Biochim. Biophys. Acta
309
243-253
1973
-
-
-
-
-
2
3
6
-
-
-
1
-
2
-
-
-
-
-
-
-
-
7
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
1
-
-
2
-
3
-
6
-
-
-
1
-
-
-
-
-
-
-
-
7
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-