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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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
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
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
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
testosterone-acetate + 2 reduced ferredoxin [iron-sulfur] cluster + O2 + 2 H+
1alpha-hydroxytestosterone acetate + H2O + 2 oxidized ferredoxin [iron-sulfur] cluster
show the reaction diagram
Escherichia coli-based whole-cell biocatalyst system
Escherichia coli-based whole-cell biocatalyst system produces a mixture (1:2.5:3) of an unknown compound and 1alpha- and 9alpha-hydroxytestosterone acetate
-
?
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
cytochrome P-450-dependent monooxygenase
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.031
androstenedione
pH and temperature not specified in the publication
0.04
testosterone
pH and temperature not specified in the publication
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50220
ESI-TOF mass spectrometry, holoenzyme
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in a soluble form in Escherichia coli
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pharmacology
modification at the C-1 position of a steroid is of pharmaceutical interest. Biotransformation can overcome tedious multistep chemical synthesis