Information on EC 1.14.15.19 - C-19 steroid 1alpha-hydroxylase

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The expected taxonomic range for this enzyme is: Sorangium cellulosum

EC NUMBER
COMMENTARY hide
1.14.15.19
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RECOMMENDED NAME
GeneOntology No.
C-19 steroid 1alpha-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
testosterone + 2 reduced ferredoxin [iron-sulfur] cluster + O2 + 2 H+ = 1alpha-hydroxytestosterone + H2O + 2 oxidized ferredoxin [iron-sulfur] cluster
show the reaction diagram
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-
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SYSTEMATIC NAME
IUBMB Comments
testosterone,reduced-ferredoxin:oxygen oxidoreductase (1alpha-hydroxylating)
The enzyme, characterized from the bacterium Sorangium cellulosum, is a class I cytochrome P-450, and uses ferredoxin as its electron donor [1]. It was shown to act on several C-19 steroid substrates, including testosterone, androstenedione, testosterone-acetate and 11-oxoandrostenedione [2].
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
A9FDB7
UniProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-nootkatone + reduced ferredoxin [iron-sulfur] cluster + O2 + H+
?
show the reaction diagram
11-oxoandrostenedione + 2 reduced ferredoxin [iron-sulfur] cluster + O2 + 2 H+
1alpha-hydroxy-11-oxoandrostenedione + H2O + 2 oxidized ferredoxin [iron-sulfur] cluster
show the reaction diagram
A9FDB7;
Escherichia coli-based whole-cell biocatalyst system
-
-
?
androstenedione + 2 reduced ferredoxin [iron-sulfur] cluster + O2 + 2 H+
1alpha-hydroxyandrostenedione + H2O + 2 oxidized ferredoxin [iron-sulfur] cluster
show the reaction diagram
A9FDB7;
Escherichia coli-based whole-cell biocatalyst system
-
-
?
androstenedione + reduced ferredoxin [iron-sulfur] cluster + O2 + H+
?
show the reaction diagram
testosterone + 2 reduced ferredoxin [iron-sulfur] cluster + O2 + 2 H+
1alpha-hydroxytestosterone + H2O + 2 oxidized ferredoxin [iron-sulfur] cluster
show the reaction diagram
testosterone + reduced ferredoxin [iron-sulfur] cluster + O2 + H+
1alpha-hydroxytestosterone + H2O + oxidized ferredoxin [iron-sulfur] cluster
show the reaction diagram
zerumbone + reduced ferredoxin [iron-sulfur] cluster + O2 + H+
?
show the reaction diagram
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
testosterone + reduced ferredoxin [iron-sulfur] cluster + O2 + H+
1alpha-hydroxytestosterone + H2O + oxidized ferredoxin [iron-sulfur] cluster
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P-450
A9FDB7;
cytochrome P-450-dependent monooxygenase
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.031
androstenedione
A9FDB7;
pH and temperature not specified in the publication
0.04
testosterone
A9FDB7;
pH and temperature not specified in the publication
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50220
A9FDB7;
ESI-TOF mass spectrometry, holoenzyme
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in a soluble form in Escherichia coli
A9FDB7;
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pharmacology
A9FDB7;
modification at the C-1 position of a steroid is of pharmaceutical interest. Biotransformation can overcome tedious multistep chemical synthesis