BRENDA - Enzyme Database show
show all sequences of 1.14.99.14

Discovery of a steroid 11alpha-hydroxylase from Rhizopus oryzae and its biotechnological application

Petric, S.; Hakki, T.; Bernhardt, R.; Zigon, D.; Cresnar, B.; J. Biotechnol. 150, 428-437 (2010)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
gene CYP509C12, cloning from a cDNA library, DNA and amino acid sequence determination and analysis, phylogenetic analysis, and recombinant expression in Pichia pastoris, coexpression with NAD(P)H-dependent reductase also from Rhizopus oryzae, which improves electron transfer to CYP509C12 and thus increases the production of 11-hydroxyprogesterone by 7fold. The engineered strain displays total bioconversion of progesterone into 11alpha-hydroxyprogesterone and small amounts of 6beta-hydroxyprogesterone
Rhizopus oryzae
Engineering
Amino acid exchange
Commentary
Organism
additional information
gene CYP509C12, production of a recombinant Pichia pastoris engieered to coexpress gene CYP509C12, ecoding the enzyme with the NAD(P)H-dependent reductase also from Rhizopus oryzae, to improve electron transfer to CYP509C12 and thus increases the production of 11-hydroxyprogesterone by 7fold. The engineered strain displays total bioconversion of progesterone into 11alpha-hydroxyprogesterone and small amounts of 6beta-hydroxyprogesterone and is useful for biotechnologic applications
Rhizopus oryzae
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
11-deoxycorticosterone + AH2 + O2
Rhizopus oryzae
-
? + A + H2O
-
-
?
11-deoxycorticosterone + AH2 + O2
Rhizopus oryzae RA 99-880
-
? + A + H2O
-
-
?
11-deoxycortisol + AH2 + O2
Rhizopus oryzae
-
? + A + H2O
-
-
?
11-deoxycortisol + AH2 + O2
Rhizopus oryzae RA 99-880
-
? + A + H2O
-
-
?
progesterone + AH2 + O2
Rhizopus oryzae
-
11alpha-hydroxyprogesterone + A + H2O
-
-
?
progesterone + AH2 + O2
Rhizopus oryzae RA 99-880
-
11alpha-hydroxyprogesterone + A + H2O
-
-
?
testosterone + AH2 + O2
Rhizopus oryzae
-
11alpha-hydroxytestosterone + A + H2O
-
-
?
testosterone + AH2 + O2
Rhizopus oryzae RA 99-880
-
11alpha-hydroxytestosterone + A + H2O
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Rhizopus oryzae
-
gene CYP509C12
-
Rhizopus oryzae RA 99-880
-
gene CYP509C12
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
11-deoxycorticosterone + AH2 + O2
-
715693
Rhizopus oryzae
? + A + H2O
-
-
-
?
11-deoxycorticosterone + AH2 + O2
-
715693
Rhizopus oryzae RA 99-880
? + A + H2O
-
-
-
?
11-deoxycortisol + AH2 + O2
-
715693
Rhizopus oryzae
? + A + H2O
-
-
-
?
11-deoxycortisol + AH2 + O2
-
715693
Rhizopus oryzae RA 99-880
? + A + H2O
-
-
-
?
additional information
hydroxylations take place predominantly at 11alpha and 6beta positions of the steroid ring system
715693
Rhizopus oryzae
?
-
-
-
-
additional information
hydroxylations take place predominantly at 11alpha and 6beta positions of the steroid ring system
715693
Rhizopus oryzae RA 99-880
?
-
-
-
-
progesterone + AH2 + O2
-
715693
Rhizopus oryzae
11alpha-hydroxyprogesterone + A + H2O
-
-
-
?
progesterone + AH2 + O2
-
715693
Rhizopus oryzae RA 99-880
11alpha-hydroxyprogesterone + A + H2O
-
-
-
?
testosterone + AH2 + O2
-
715693
Rhizopus oryzae
11alpha-hydroxytestosterone + A + H2O
-
-
-
?
testosterone + AH2 + O2
-
715693
Rhizopus oryzae RA 99-880
11alpha-hydroxytestosterone + A + H2O
-
-
-
?
Cloned(Commentary) (protein specific)
Commentary
Organism
gene CYP509C12, cloning from a cDNA library, DNA and amino acid sequence determination and analysis, phylogenetic analysis, and recombinant expression in Pichia pastoris, coexpression with NAD(P)H-dependent reductase also from Rhizopus oryzae, which improves electron transfer to CYP509C12 and thus increases the production of 11-hydroxyprogesterone by 7fold. The engineered strain displays total bioconversion of progesterone into 11alpha-hydroxyprogesterone and small amounts of 6beta-hydroxyprogesterone
Rhizopus oryzae
Engineering (protein specific)
Amino acid exchange
Commentary
Organism
additional information
gene CYP509C12, production of a recombinant Pichia pastoris engieered to coexpress gene CYP509C12, ecoding the enzyme with the NAD(P)H-dependent reductase also from Rhizopus oryzae, to improve electron transfer to CYP509C12 and thus increases the production of 11-hydroxyprogesterone by 7fold. The engineered strain displays total bioconversion of progesterone into 11alpha-hydroxyprogesterone and small amounts of 6beta-hydroxyprogesterone and is useful for biotechnologic applications
Rhizopus oryzae
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
11-deoxycorticosterone + AH2 + O2
Rhizopus oryzae
-
? + A + H2O
-
-
?
11-deoxycorticosterone + AH2 + O2
Rhizopus oryzae RA 99-880
-
? + A + H2O
-
-
?
11-deoxycortisol + AH2 + O2
Rhizopus oryzae
-
? + A + H2O
-
-
?
11-deoxycortisol + AH2 + O2
Rhizopus oryzae RA 99-880
-
? + A + H2O
-
-
?
progesterone + AH2 + O2
Rhizopus oryzae
-
11alpha-hydroxyprogesterone + A + H2O
-
-
?
progesterone + AH2 + O2
Rhizopus oryzae RA 99-880
-
11alpha-hydroxyprogesterone + A + H2O
-
-
?
testosterone + AH2 + O2
Rhizopus oryzae
-
11alpha-hydroxytestosterone + A + H2O
-
-
?
testosterone + AH2 + O2
Rhizopus oryzae RA 99-880
-
11alpha-hydroxytestosterone + A + H2O
-
-
?
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
11-deoxycorticosterone + AH2 + O2
-
715693
Rhizopus oryzae
? + A + H2O
-
-
-
?
11-deoxycorticosterone + AH2 + O2
-
715693
Rhizopus oryzae RA 99-880
? + A + H2O
-
-
-
?
11-deoxycortisol + AH2 + O2
-
715693
Rhizopus oryzae
? + A + H2O
-
-
-
?
11-deoxycortisol + AH2 + O2
-
715693
Rhizopus oryzae RA 99-880
? + A + H2O
-
-
-
?
additional information
hydroxylations take place predominantly at 11alpha and 6beta positions of the steroid ring system
715693
Rhizopus oryzae
?
-
-
-
-
additional information
hydroxylations take place predominantly at 11alpha and 6beta positions of the steroid ring system
715693
Rhizopus oryzae RA 99-880
?
-
-
-
-
progesterone + AH2 + O2
-
715693
Rhizopus oryzae
11alpha-hydroxyprogesterone + A + H2O
-
-
-
?
progesterone + AH2 + O2
-
715693
Rhizopus oryzae RA 99-880
11alpha-hydroxyprogesterone + A + H2O
-
-
-
?
testosterone + AH2 + O2
-
715693
Rhizopus oryzae
11alpha-hydroxytestosterone + A + H2O
-
-
-
?
testosterone + AH2 + O2
-
715693
Rhizopus oryzae RA 99-880
11alpha-hydroxytestosterone + A + H2O
-
-
-
?
Expression
Organism
Commentary
Expression
Rhizopus oryzae
CYP509C12 expression is induced by progesterone
up
Expression (protein specific)
Organism
Commentary
Expression
Rhizopus oryzae
CYP509C12 expression is induced by progesterone
up
Other publictions for EC 1.14.99.14
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)
745647
Wang
Cloning and identification of ...
Absidia caerulea, Absidia caerulea AS3.65
J. Steroid Biochem. Mol. Biol.
171
254-261
2017
-
-
1
-
-
-
1
-
-
-
-
-
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7
-
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-
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-
4
1
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1
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1
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4
1
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-
746508
Gao
Screening for strains with 11 ...
Aspergillus ochraceus, Aspergillus ochraceus CICC41473, Beauveria bassiana, Beauveria bassiana ACCC30728, Cunninghamella elegans, Cunninghamella elegans CICC40250, Metarhizium anisopliae, Metarhizium anisopliae ACCC30194, Rhizopus stolonifer, Rhizopus stolonifer CGMCC33900
Steroids
124
67-71
2017
-
-
-
-
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-
-
-
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10
-
10
-
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10
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10
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-
-
744807
Chen
Molecular cloning, expression ...
Rhizopus oryzae, Rhizopus oryzae CICC 40467
Enzyme Microb. Technol.
66
28-34
2014
-
-
1
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-
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2
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2
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2
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727305
Nguyen
Changing the regioselectivity ...
Bacillus megaterium
ChemBioChem
13
1161-1166
2012
-
1
-
-
15
-
-
14
1
-
1
2
-
1
-
-
-
-
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3
1
1
-
-
15
-
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1
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-
15
-
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-
14
1
-
1
2
-
-
-
-
-
-
-
-
3
1
1
-
-
15
-
-
-
-
-
-
-
-
15
15
715693
Petric
Discovery of a steroid 11alpha ...
Rhizopus oryzae, Rhizopus oryzae RA 99-880
J. Biotechnol.
150
428-437
2010
-
-
1
-
1
-
-
-
-
-
-
8
-
3
-
-
-
-
-
-
-
-
10
-
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1
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1
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8
-
-
-
-
-
-
-
-
10
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
438363
Kunic
Comparison of two monooxygenas ...
Rhizopus stolonifer
Pflugers Arch.
439
R107-108
2000
-
-
-
-
-
-
2
-
1
-
-
1
-
1
-
-
-
-
-
-
-
-
2
-
-
-
-
-
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-
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1
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1
-
-
-
-
2
-
-
1
-
-
1
-
-
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-
-
2
-
-
-
-
-
-
-
-
-
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-
-
-
-
438362
Dutta
Bioconversion of progesterone ...
Aspergillus ochraceus, Aspergillus ochraceus G8, Aspergillus ochraceus TS, Rhizopus stolonifer
Curr. Microbiol.
39
309-312
1999
9
-
-
-
-
1
-
-
-
-
-
4
-
7
-
-
-
-
-
4
-
-
4
-
-
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-
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9
-
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-
-
1
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-
-
-
-
-
-
4
-
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-
4
-
-
4
-
-
-
-
-
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-
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-
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-
-
-
-
438361
Lenasi
Identification and partial cha ...
Rhizopus stolonifer
Arch. Biochem. Biophys.
330
80-86
1996
-
-
-
-
-
1
-
-
1
-
-
1
-
1
-
-
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-
1
-
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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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1
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1
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1
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1
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
438360
Bonnerjea
Poly(ethylene glycol) precipit ...
Rhizopus stolonifer
Appl. Microbiol. Biotechnol.
27
362-365
1988
-
1
-
-
-
-
-
-
3
-
-
1
-
1
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1
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3
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1
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3
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1
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1
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3
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-
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-
438359
Broad
Studies for the large scale is ...
Rhizopus stolonifer
Enzyme Microb. Technol.
9
546-548
1986
-
1
-
-
-
-
-
-
2
-
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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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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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-
-
-
-
-
-
-
-
-
-
-
-
-
438358
Cresnar
Resolution and reconstitution ...
Rhizopus stolonifer
Biochem. Biophys. Res. Commun.
133
1057-1063
1985
-
-
-
-
-
-
-
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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
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
1
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-
288562
Jayanthi
Microsomal 11alpha-hydroxylati ...
Aspergillus ochraceus, Aspergillus ochraceus NRRL 405, Aspergillus ochraceus TS, Rhizopus oryzae, Rhizopus stolonifer
Biochem. Biophys. Res. Commun.
106
1262-1268
1982
-
-
-
-
-
-
7
-
4
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5
-
9
-
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-
2
2
-
8
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1
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5
-
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5
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7
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4
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5
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2
2
-
8
-
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1
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-
-
-
-
438356
Ghosh
11alpha-Hydroxylation of proge ...
Aspergillus ochraceus, Aspergillus ochraceus TS
J. Steroid Biochem.
14
1063-1067
1981
2
-
-
-
-
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1
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2
-
5
-
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2
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1
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1
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1
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2
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-
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-
438355
Hanisch
-
Regeneration of the progestero ...
Rhizopus stolonifer
Biotechnol. Lett.
2
123-126
1980
-
-
-
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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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1
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-
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-
-
-
-
438354
Shibahara
Microbial hydroxylations. V. 1 ...
Aspergillus ochraceus, Aspergillus ochraceus NRRL 405, Bacillus megaterium
Biochim. Biophys. Acta
202
172-179
1979
3
-
-
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3
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4
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1
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9
-
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1
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3
-
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3
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1
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9
-
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1
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