BRENDA - Enzyme Database
show all sequences of 1.3.99.4

Crystal structure and site-directed mutagenesis of 3-ketosteroid Delta1-dehydrogenase from Rhodococcus erythropolis SQ1 explain its catalytic mechanism

Rohman, A.; van Oosterwijk, N.; Thunnissen, A.M.; Dijkstra, B.W.; J. Biol. Chem. 288, 35559-35568 (2013)

Data extracted from this reference:

Cloned(Commentary)
Cloned (Commentary)
Organism
-
Rhodococcus erythropolis
Crystallization (Commentary)
Crystallization (Commentary)
Organism
in complex with the reaction product 1,4-androstadiene-3,17-dione, to 2.3 A resolution. Key active site residues are Tyr119, Tyr318, Tyr487, and Gly491
Rhodococcus erythropolis
Engineering
Protein Variants
Commentary
Organism
Y119F
almost complete loss of activity
Rhodococcus erythropolis
Y318F
almost complete loss of activity
Rhodococcus erythropolis
Y487F
almost complete loss of activity
Rhodococcus erythropolis
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.037
-
4-androstene-3,17-dione
wild-type, pH 8.0, 22°C
Rhodococcus erythropolis
0.193
-
4-androstene-3,17-dione
mutant Y487F, pH 8.0, 22°C
Rhodococcus erythropolis
0.335
-
4-androstene-3,17-dione
mutant Y119F, pH 8.0, 22°C
Rhodococcus erythropolis
Organism
Organism
UniProt
Commentary
Textmining
Rhodococcus erythropolis
Q9RA02
-
-
Rhodococcus erythropolis SQ1
Q9RA02
-
-
Specific Activity [micromol/min/mg]
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
72.9
-
pH 8.0, 22°C
Rhodococcus erythropolis
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
4-androstene-3,17-dione + 2,6-dichlorophenol-indophenol
-
742850
Rhodococcus erythropolis
1,4-androstadiene-3,17-dione + reduced 2,6-dichlorophenol-indophenol
-
-
-
?
4-androstene-3,17-dione + 2,6-dichlorophenol-indophenol
-
742850
Rhodococcus erythropolis SQ1
1,4-androstadiene-3,17-dione + reduced 2,6-dichlorophenol-indophenol
-
-
-
?
9alpha-hydroxy-4-androstene-3,17-dione + 2,6-dichlorophenol-indophenol
-
742850
Rhodococcus erythropolis
9alpha-hydroxy-androst-1,4-diene-3,17-dione + reduced 2,6-dichlorophenol-indophenol
-
-
-
?
9alpha-hydroxy-4-androstene-3,17-dione + 2,6-dichlorophenol-indophenol
-
742850
Rhodococcus erythropolis SQ1
9alpha-hydroxy-androst-1,4-diene-3,17-dione + reduced 2,6-dichlorophenol-indophenol
-
-
-
?
additional information
in catalytic mechanism Tyr487 and Gly491 work in tandem to promote keto-enol tautomerization and increase the acidity of the C2 hydrogen atoms of the substrate. With assistance of Tyr119, the general base Tyr318 abstracts the axialbeta-hydrogen from C2 as a proton, whereas the FAD accepts the axial alpha-hydrogen from the C1 atom of the substrate as a hydride ion
742850
Rhodococcus erythropolis
?
-
-
-
-
additional information
in catalytic mechanism Tyr487 and Gly491 work in tandem to promote keto-enol tautomerization and increase the acidity of the C2 hydrogen atoms of the substrate. With assistance of Tyr119, the general base Tyr318 abstracts the axialbeta-hydrogen from C2 as a proton, whereas the FAD accepts the axial alpha-hydrogen from the C1 atom of the substrate as a hydride ion
742850
Rhodococcus erythropolis SQ1
?
-
-
-
-
Synonyms
Synonyms
Commentary
Organism
DELTA1-KSTD1
-
Rhodococcus erythropolis
KSTD1
-
Rhodococcus erythropolis
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.036
-
4-androstene-3,17-dione
mutant Y119F, pH 8.0, 22°C
Rhodococcus erythropolis
1.7
-
4-androstene-3,17-dione
mutant Y487F, pH 8.0, 22°C
Rhodococcus erythropolis
68.1
-
4-androstene-3,17-dione
wild-type, pH 8.0, 22°C
Rhodococcus erythropolis
Cofactor
Cofactor
Commentary
Organism
Structure
FAD
the C1 and C2 atoms of the substrate are at reaction distance to the N5 atom of the isoalloxazine ring of FAD and the hydroxyl group of Tyr318, respectively, whereas the C3 carbonyl group is at hydrogen bonding distance from the hydroxyl group of Tyr487 and the backbone amide of Gly491
Rhodococcus erythropolis
Cloned(Commentary) (protein specific)
Commentary
Organism
-
Rhodococcus erythropolis
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
FAD
the C1 and C2 atoms of the substrate are at reaction distance to the N5 atom of the isoalloxazine ring of FAD and the hydroxyl group of Tyr318, respectively, whereas the C3 carbonyl group is at hydrogen bonding distance from the hydroxyl group of Tyr487 and the backbone amide of Gly491
Rhodococcus erythropolis
Crystallization (Commentary) (protein specific)
Crystallization
Organism
in complex with the reaction product 1,4-androstadiene-3,17-dione, to 2.3 A resolution. Key active site residues are Tyr119, Tyr318, Tyr487, and Gly491
Rhodococcus erythropolis
Engineering (protein specific)
Protein Variants
Commentary
Organism
Y119F
almost complete loss of activity
Rhodococcus erythropolis
Y318F
almost complete loss of activity
Rhodococcus erythropolis
Y487F
almost complete loss of activity
Rhodococcus erythropolis
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.037
-
4-androstene-3,17-dione
wild-type, pH 8.0, 22°C
Rhodococcus erythropolis
0.193
-
4-androstene-3,17-dione
mutant Y487F, pH 8.0, 22°C
Rhodococcus erythropolis
0.335
-
4-androstene-3,17-dione
mutant Y119F, pH 8.0, 22°C
Rhodococcus erythropolis
Specific Activity [micromol/min/mg] (protein specific)
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
72.9
-
pH 8.0, 22°C
Rhodococcus erythropolis
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
4-androstene-3,17-dione + 2,6-dichlorophenol-indophenol
-
742850
Rhodococcus erythropolis
1,4-androstadiene-3,17-dione + reduced 2,6-dichlorophenol-indophenol
-
-
-
?
4-androstene-3,17-dione + 2,6-dichlorophenol-indophenol
-
742850
Rhodococcus erythropolis SQ1
1,4-androstadiene-3,17-dione + reduced 2,6-dichlorophenol-indophenol
-
-
-
?
9alpha-hydroxy-4-androstene-3,17-dione + 2,6-dichlorophenol-indophenol
-
742850
Rhodococcus erythropolis
9alpha-hydroxy-androst-1,4-diene-3,17-dione + reduced 2,6-dichlorophenol-indophenol
-
-
-
?
9alpha-hydroxy-4-androstene-3,17-dione + 2,6-dichlorophenol-indophenol
-
742850
Rhodococcus erythropolis SQ1
9alpha-hydroxy-androst-1,4-diene-3,17-dione + reduced 2,6-dichlorophenol-indophenol
-
-
-
?
additional information
in catalytic mechanism Tyr487 and Gly491 work in tandem to promote keto-enol tautomerization and increase the acidity of the C2 hydrogen atoms of the substrate. With assistance of Tyr119, the general base Tyr318 abstracts the axialbeta-hydrogen from C2 as a proton, whereas the FAD accepts the axial alpha-hydrogen from the C1 atom of the substrate as a hydride ion
742850
Rhodococcus erythropolis
?
-
-
-
-
additional information
in catalytic mechanism Tyr487 and Gly491 work in tandem to promote keto-enol tautomerization and increase the acidity of the C2 hydrogen atoms of the substrate. With assistance of Tyr119, the general base Tyr318 abstracts the axialbeta-hydrogen from C2 as a proton, whereas the FAD accepts the axial alpha-hydrogen from the C1 atom of the substrate as a hydride ion
742850
Rhodococcus erythropolis SQ1
?
-
-
-
-
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.036
-
4-androstene-3,17-dione
mutant Y119F, pH 8.0, 22°C
Rhodococcus erythropolis
1.7
-
4-androstene-3,17-dione
mutant Y487F, pH 8.0, 22°C
Rhodococcus erythropolis
68.1
-
4-androstene-3,17-dione
wild-type, pH 8.0, 22°C
Rhodococcus erythropolis
KCat/KM [mM/s]
kcat/KM Value [1/mMs-1]
kcat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
0.108
-
4-androstene-3,17-dione
mutant Y119F, pH 8.0, 22°C
Rhodococcus erythropolis
9.1
-
4-androstene-3,17-dione
mutant Y487F, pH 8.0, 22°C
Rhodococcus erythropolis
1838
-
4-androstene-3,17-dione
wild-type, pH 8.0, 22°C
Rhodococcus erythropolis
KCat/KM [mM/s] (protein specific)
KCat/KM Value [1/mMs-1]
KCat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
0.108
-
4-androstene-3,17-dione
mutant Y119F, pH 8.0, 22°C
Rhodococcus erythropolis
9.1
-
4-androstene-3,17-dione
mutant Y487F, pH 8.0, 22°C
Rhodococcus erythropolis
1838
-
4-androstene-3,17-dione
wild-type, pH 8.0, 22°C
Rhodococcus erythropolis
Other publictions for EC 1.3.99.4
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
Synonyms
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)
743236
Guevara
Functional differentiation of ...
Rhodococcus ruber, Rhodococcus ruber Chol-4
Microb. Cell Fact.
16
42
2017
-
-
-
-
-
-
-
20
-
-
-
-
-
7
-
-
-
-
-
-
-
-
33
1
3
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
20
-
-
-
-
-
-
-
-
-
-
-
-
33
3
-
-
-
-
-
-
-
-
-
-
-
-
-
-
743031
Shao
A mutant form of 3-ketosteroi ...
Mycolicibacterium neoaurum, Mycolicibacterium neoaurum JC-12, Mycolicibacterium neoaurum ST-095
J. Ind. Microbiol. Biotechnol.
43
691-701
2016
-
-
1
-
1
-
-
2
-
-
-
-
-
4
-
-
-
-
-
-
1
-
3
1
-
-
-
-
2
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
1
-
3
1
-
-
-
2
-
-
-
-
-
-
-
-
2
2
743221
Yao
Characterization and engineer ...
Mycolicibacterium neoaurum, Mycolicibacterium neoaurum ATCC 25795
Metab. Eng.
24
181-191
2014
-
1
1
-
-
-
-
14
-
-
-
-
-
6
-
-
-
-
-
-
-
-
28
1
3
-
-
-
-
-
-
-
-
-
-
-
-
3
3
-
-
-
-
-
-
-
14
-
-
-
-
-
-
-
-
-
-
-
-
28
3
-
-
-
-
-
-
-
-
-
-
-
-
-
-
724670
Brzezinska
The role of 3-ketosteroid 1(2) ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
BMC Microbiol.
13
43
2013
-
-
-
-
-
-
-
-
-
-
-
-
-
175
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
1
1
1
-
-
725830
Zhang
Bioconversion of 4-androstene- ...
Mycolicibacterium neoaurum, Mycolicibacterium neoaurum JC-12
J. Steroid Biochem. Mol. Biol.
135
36-42
2013
-
-
1
-
-
-
-
-
-
-
-
2
-
3
-
-
-
-
-
-
1
-
4
-
2
1
-
-
-
1
-
-
1
-
-
-
-
-
1
1
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
1
-
4
-
1
-
-
-
1
-
-
-
-
1
1
-
-
-
742850
Rohman
Crystal structure and site-di ...
Rhodococcus erythropolis, Rhodococcus erythropolis SQ1
J. Biol. Chem.
288
35559-35568
2013
-
-
1
1
3
-
-
3
-
-
-
-
-
4
-
-
-
-
-
-
1
-
6
-
2
-
-
-
3
-
-
-
1
-
-
-
-
-
1
1
1
3
-
-
-
-
3
-
-
-
-
-
-
-
-
-
-
1
-
6
-
-
-
-
3
-
-
-
-
-
-
-
-
3
3
723868
Rohman
Purification, crystallization ...
Rhodococcus erythropolis, Rhodococcus erythropolis SQ1
Acta Crystallogr. Sect. F
68
551-556
2012
-
-
1
1
-
-
-
-
-
-
1
2
-
4
-
-
1
-
-
-
-
-
2
1
2
-
-
-
-
-
-
1
1
-
-
-
-
-
1
1
1
-
-
-
-
-
-
-
-
1
2
-
-
-
1
-
-
-
-
2
1
-
-
-
-
-
-
1
-
-
1
1
-
-
-
724074
Chen
Characterization and applicati ...
Aspergillus fumigatus, Aspergillus fumigatus CICC 40167
Appl. Microbiol. Biotechnol.
96
133-142
2012
-
1
1
-
-
-
-
-
1
-
1
2
-
2
-
-
1
-
-
-
-
-
2
1
3
1
-
-
-
1
-
-
2
-
1
-
-
1
1
2
-
-
-
-
-
-
-
1
-
1
2
-
-
-
1
-
-
-
-
2
1
1
-
-
-
1
-
-
1
-
1
1
-
-
-
724000
Wei
Inactivation and augmentation ...
Mycolicibacterium neoaurum, Mycolicibacterium neoaurum NwIB-01
Appl. Environ. Microbiol.
76
4578-4582
2010
-
1
1
-
-
-
-
-
-
-
-
2
-
2
-
-
1
-
-
-
1
-
6
-
3
1
-
-
-
1
-
-
1
-
-
-
-
1
1
1
-
-
-
-
-
-
-
-
-
-
2
-
-
-
1
-
-
1
-
6
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
684994
Knol
3-Keto-5alpha-steroid DELTA(1) ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv, Rhodococcus erythropolis, Rhodococcus erythropolis SQ1
Biochem. J.
410
339-346
2008
-
-
1
-
-
1
-
23
-
-
3
-
-
184
-
-
1
-
-
-
-
-
49
-
13
-
-
-
-
-
-
-
-
-
-
-
-
-
3
-
-
-
1
-
-
-
23
-
-
3
-
-
-
-
1
-
-
-
-
49
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
688748
Li
Expression of ksdD gene encodi ...
Pimelobacter simplex
Lett. Appl. Microbiol.
44
563-568
2007
-
-
1
-
-
-
-
-
-
-
1
-
-
4
-
-
-
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-
-
2
-
1
-
2
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1
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1
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2
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
675829
Brzostek
Identification and targeted di ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Ra / ATCC 25177, Mycolicibacterium smegmatis, Mycolicibacterium smegmatis mc(2)155 / ATCC 700084
Microbiology
151
2393-2402
2005
-
2
2
-
1
-
-
-
-
-
-
-
-
31
-
-
-
-
-
-
-
-
2
-
5
-
-
-
-
-
-
-
1
-
-
-
-
2
2
1
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
654270
Horinouchi
A new bacterial steroid degrad ...
Comamonas testosteroni, Comamonas testosteroni TA441
Appl. Environ. Microbiol.
69
4421-4430
2003
-
-
-
-
-
-
-
-
-
-
-
2
-
2
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
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2
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2
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-
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-
-
-
-
-
-
-
-
657152
Adham
-
Biochemical studies on the mic ...
Pseudomonas fluorescens
Proc. Biochem.
38
897-902
2003
1
-
-
-
-
-
5
-
-
6
-
-
-
1
-
-
-
-
-
-
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-
1
-
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1
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5
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6
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1
-
-
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-
-
-
-
-
-
-
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-
-
-
-
656722
van der Geize
Molecular and functional chara ...
Rhodococcus erythropolis, Rhodococcus erythropolis SQ1
Microbiology
148
3285-3292
2002
-
-
1
-
2
-
-
2
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8
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1
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391391
Van der Geize
Unmarked gene deletion mutagen ...
Rhodococcus erythropolis
FEMS Microbiol. Lett.
205
197-202
2001
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-
1
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6
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391394
Fujii
Essential tyrosine residues in ...
Rhodococcus rhodochrous
J. Biochem.
126
662-667
1999
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-
1
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-
1
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-
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-
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1
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391396
Morii
3-Ketosteroid-DELTA1-dehydroge ...
Rhodococcus rhodochrous
J. Biochem.
124
1026-1032
1998
-
-
1
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-
1
1
-
1
-
-
5
-
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1
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391392
Choi
Purification and characterizat ...
Pimelobacter simplex
J. Biochem.
117
1043-1049
1995
-
-
-
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5
1
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1
-
1
1
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1
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1
5
1
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1
1
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1
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5
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1
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1
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1
5
1
1
1
-
-
1
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391393
Choi
Secretory overproduction of Ar ...
Pimelobacter simplex
Appl. Microbiol. Biotechnol.
43
1044-1049
1995
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1
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391395
Molnar
Molecular cloning, expression ...
Pimelobacter simplex
Mol. Microbiol.
15
895-905
1995
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-
1
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1
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1
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391375
Itagaki
Purification and characterizat ...
Gordonia rubripertincta
Biochim. Biophys. Acta
1038
60-67
1990
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-
-
-
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-
2
11
-
-
1
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1
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1
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1
1
15
1
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1
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2
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2
2
-
1
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1
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2
-
11
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1
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1
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1
1
15
1
1
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2
-
2
2
-
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391378
Itagaki
Spectral properties of 3-ketos ...
Gordonia rubripertincta
Biochim. Biophys. Acta
1040
281-286
1990
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1
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1
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2
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391379
Kloosterman IV
-
Effect of supersaturated aqueo ...
Pimelobacter simplex
Enzyme Microb. Technol.
6
113-116
1984
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1
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1
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-
391385
Udvardy
-
Kinetics of the formation of s ...
Pimelobacter simplex
FEMS Symp.
13
21-33
1982
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1
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391384
Atrat
Steroid transformation with im ...
Mycolicibacterium phlei, Nocardia erythropolis, Rhodococcus opacus
Z. Allg. Mikrobiol.
21
3-6
1981
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3
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3
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3
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391376
Atrat
-
Efficient purification of a mi ...
Rhodococcus opacus
J. Chromatogr.
189
279-283
1980
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-
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1
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1
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1
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-
391389
Hörhold
Steroid transforming enzymes i ...
Rhodococcus opacus
Z. Allg. Mikrobiol.
20
23-32
1980
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1
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-
391377
Groh
Steroid-transforming enzymes f ...
Rhodococcus opacus
Z. Allg. Mikrobiol.
19
727-730
1979
-
-
-
-
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3
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2
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2
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-
391388
Hörhold
Steroid-transforming enzymes f ...
Rhodococcus opacus
Z. Allg. Mikrobiol.
19
731-739
1979
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1
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391387
Lestrovaja
Steroid transforming enzymes f ...
Rhodococcus opacus
Z. Allg. Mikrobiol.
18
189-196
1978
-
-
-
-
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-
1
1
-
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1
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1
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1
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2
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1
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1
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1
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1
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1
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1
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2
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-
391390
Abul-Hajj
Isolation of vitamin K2(35) fr ...
Ilyonectria destructans, Pimelobacter simplex, Plectosphaerella cucumerina, Rhodococcus hoagii
J. Biol. Chem.
253
2356-2360
1978
-
-
-
-
-
-
-
-
-
-
-
-
-
4
-
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15
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15
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391386
Hörhold
Steroid-transforming enzymes f ...
Rhodococcus opacus
Z. Allg. Mikrobiol.
16
559-561
1976
-
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-
-
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-
-
1
-
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1
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1
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-
391380
Penasse
The active center of the 3-oxo ...
Pimelobacter simplex
Eur. J. Biochem.
47
555-559
1974
-
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1
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1
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1
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1
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1
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391382
Rodig
The stereochemistry of hydroge ...
Saccharomyces cerevisiae
Biochem. Biophys. Res. Commun.
56
467-470
1974
-
-
-
-
-
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-
2
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1
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1
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1
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-
391381
Aries
-
Degradation of steroids by int ...
Clostridium paraputrificum
Biochim. Biophys. Acta
248
482-488
1971
-
-
-
-
-
-
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-
-
-
-
-
1
-
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5
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1
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5
-
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1
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-
-
-
-
-
-
-
391383
Levy
Bacterial oxidation of steroid ...
Comamonas testosteroni
J. Biol. Chem.
234
2014-2021
1959
-
-
-
-
-
-
8
-
1
-
-
-
-
1
-
-
1
-
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-
-
-
9
-
-
1
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1
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8
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1
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1
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9
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1
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1
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