1.14.15.8: steroid 15beta-monooxygenase
This is an abbreviated version!
For detailed information about steroid 15beta-monooxygenase, go to the full flat file.
Word Map on EC 1.14.15.8
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1.14.15.8
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megaterium
-
p-450-dependent
-
ferredoxins
-
synthesis
-
adrenodoxin
-
autologous
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triterpene
-
11-oxidase
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testosterone
-
flavodoxin
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flavoprotein
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hydroxylases
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aniline
-
11-deoxycortisol
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nadph-dependent
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fmn-containing
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paramagnetic
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iron-sulfur
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biocatalyst
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11-keto
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11-deoxycorticosterone
- 1.14.15.8
- megaterium
-
p-450-dependent
- ferredoxins
- synthesis
- adrenodoxin
-
autologous
-
triterpene
-
11-oxidase
- testosterone
- flavodoxin
- flavoprotein
- hydroxylases
- aniline
- 11-deoxycortisol
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nadph-dependent
-
fmn-containing
-
paramagnetic
-
iron-sulfur
-
biocatalyst
-
11-keto
- 11-deoxycorticosterone
Reaction
Synonyms
15beta-hydroxylase, 15beta-hydroxylase CYP106A2, BmCYP106A2, Cyp106A1, CYP106A2, cytochrome P-450meg, cytochrome P450meg, steroid-15-beta-monooxygenase
ECTree
1.14.15.8 steroid 15beta-monooxygenaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 1.14.15.8 - steroid 15beta-monooxygenase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
11-deoxycorticosterone + reduced adrenodoxin + O2
15beta-hydroxy-11-deoxycorticosterone + 7beta,15beta-dihydroxy-11-deoxycorticosterone + oxidized adrenodoxin + H2O
-
-
-
?
11-deoxycorticosterone + reduced adrenodoxin + O2
15beta-hydroxy-11-deoxycorticosterone + oxidized adrenodoxin + H2O
11-deoxycorticosterone + reduced ferredoxin + O2
15beta-hydroxy-11-deoxycorticosterone + oxidized ferredoxin + H2O
ferredoxin from the cyanobacterium Anabaena PCC 7119
-
-
?
11-deoxycorticosterone + reduced flavodoxin + O2
15beta-hydroxy-11-deoxycorticosterone + oxidized flavodoxin + H2O
flavodoxin from the cyanobacterium Anabaena PCC 7119
-
-
?
11-deoxycorticosterone + reduced megaredoxin + O2
15beta-hydroxy-11-deoxycorticosterone + oxidized megaredoxin + H2O
-
megaredoxin is an iron-sulfur protein of Bacillus megaterium, megaredoxin has an apparent sulfur to iron ratio of 0.98
-
-
?
11-deoxycortisol + reduced adrenodoxin + O2
15beta-15,17,21-trihydroxypregn-4-ene-3,20-dione + oxidized adrenodoxin + H2O
adrenodoxin is a [2Fe-2S] ferredoxin involved in electron transfer from NADPH+ (via a reductase) to cytochrome P-450 in the adrenal gland
-
-
?
11-deoxycortisol + reduced adrenodoxin + O2
15beta-hydroxy-11-deoxycortisol + oxidized adrenodoxin + H2O
-
-
-
?
11-oxo-beta-boswellic acid + reduced ferredoxin + O2
(3alpha,15beta)-3,15-dihydroxy-11-oxours-12-en-24-oic acid + H2O
11beta-hydroxy-4-androstene-3,17-dione + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
-
-
-
?
17alpha-hydroxyprogesterone + reduced megaredoxin + O2
(15beta,17alpha)-15,17-dihydroxyprogesterone + oxidized megaredoxin + H2O
-
megaredoxin is an iron-sulfur protein of Bacillus megaterium, megaredoxin has an apparent sulfur to iron ratio of 0.98
-
-
?
17alpha-methyltestosterone + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
-
-
-
?
19-nortestosterone + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
-
-
-
?
20alpha-dihydroprogesterone + reduced megaredoxin + O2
(15beta,20alpha)-15-hydroxy-20-dihydroprogesterone + oxidized megaredoxin + H2O
-
megaredoxin is an iron-sulfur protein of Bacillus megaterium, megaredoxin has an apparent sulfur to iron ratio of 0.98
-
-
?
4-androstene-3,17-dione + reduced adrenodoxin + O2
15beta-hydroxyandrostene-3,17-dione + oxidized adrenodoxin + H2O
-
-
-
?
4-androstene-3,17-dione + reduced ferredoxin + O2
15beta-hydroxyandrost-4-en-3,17-dione + oxidized ferredoxin + H2O
Bacillus sp. PAMC 23377
-
Kd value of androstenedione is 0.387 mM
-
-
?
4-androstene-3,17-dione + reduced megaredoxin + O2
15beta-hydroxyandrostene-3,17-dione + oxidized megaredoxin + H2O
-
megaredoxin is an iron-sulfur protein of Bacillus megaterium, megaredoxin has an apparent sulfur to iron ratio of 0.98
-
-
?
6alpha-fluoro-16alpha-methyl-deoxycorticosterone + reduced ferredoxin + O2
15beta-hydroxy-6alpha-fluoro-16alpha-methyl-deoxycorticosterone + oxidized ferredoxin + H2O
-
-
-
?
abietic acid + reduced adrenodoxin + O2
12-hydroxyabietic acid + oxidized adrenodoxin + H2O
-
-
-
-
?
abietic acid + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
binding of abietic acid results in a type II difference spectrum typical for nitrogenous inhibitors
-
-
?
corticosterone + reduced adrenodoxin + O2
15beta-hydroxycorticosterone + oxidized adrenodoxin + H2O
-
-
-
?
corticosterone + reduced megaredoxin + O2
15beta-hydroxycorticosterone + oxidized megaredoxin + H2O
-
megaredoxin is an iron-sulfur protein of Bacillus megaterium, preferred substrate, megaredoxin has an apparent sulfur to iron ratio of 0.98
-
-
?
cortisone + reduced adrenodoxin + O2
15beta-hydroxycortisone + oxidized adrenodoxin + H2O
-
-
-
?
dehydroabietic acid + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
-
-
-
?
dehydroepiandrosterone + reduced adrenodoxin + O2
7beta-hydroxy-dehydroepiandrosterone + oxidized adrenodoxin + H2O
-
-
-
?
deoxycorticosterone + reduced ferredoxin + O2
15beta-hydroxy-11-deoxycorticosterone + oxidized ferredoxin + H2O
-
-
-
r
deoxycorticosterone + reduced flavodoxin + O2
15beta-hydroxy-11-deoxycorticosterone + oxidized flavodoxin + H2O
-
-
-
r
dexamethasone + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
-
-
-
?
digitoxigenin + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
-
-
-
?
imipramine + reduced adrenodoxin + O2
desipramine + oxidized adrenodoxin + H2O
-
-
-
-
?
isopimaric acid + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
-
-
-
?
nandrolone + reduced ferredoxin + O2
? + oxidized ferredoxin + H2O
Bacillus sp. PAMC 23377
-
-
-
-
?
prednisolone + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
-
-
-
?
prednisone + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
-
-
-
?
pregnenolone + reduced adrenodoxin + O2
7beta-hydroxy-pregnenolone + oxidized adrenodoxin + H2O
-
-
-
?
progesterone + reduced adrenodoxin + O2
15beta-hydroxy-progesterone + 11alpha-hydroxy-progesterone + oxidized adrenodoxin + H2O
-
-
-
?
progesterone + reduced adrenodoxin + O2
15beta-hydroxy-progesterone + oxidized adrenodoxin + H2O
adrenodoxin is a [2Fe-2S] ferredoxin involved in electron transfer from NADPH+ (via a reductase) to cytochrome P-450 in the adrenal gland, 15beta-hydroxy-progesterone is the main product of wild-type enzyme and all mutants. In order to gain insights into the structure and function of CYP106A2, whose crystal structure is unknown, a homology model has been created. The substrate progesterone is then docked into the active site to predict which residues might affect substrate binding. The model is substantiated by using a combination of theoretical and experimental investigations
-
-
?
progesterone + reduced adrenodoxin + O2
15beta-hydroxyprogesterone + oxidized adrenodoxin + H2O
progesterone + reduced ferredoxin + O2
15beta-hydroxy-progesterone + oxidized ferredoxin + H2O
Bacillus megaterium ferredoxin may be replaced by adrenal ferredoxin
-
-
?
progesterone + reduced megaredoxin + O2
15beta-hydroxyprogesterone + oxidized megaredoxin + H2O
testosterone + reduced acceptor + O2
15beta-hydroxytestosterone + oxidized acceptor + H2O
-
the major product is identified as 15beta-hydroxytestosterone. 6beta-Hydroxytestosterone and androst-4-ene-3,17-dione are present as minor products
-
-
?
testosterone + reduced adrenodoxin + O2
15beta-hydroxytestosterone + oxidized adrenodoxin + H2O
-
-
-
?
testosterone + reduced megaredoxin + O2
15beta-hydroxytestosterone + oxidized megaredoxin + H2O
-
megaredoxin is an iron-sulfur protein of Bacillus megaterium, megaredoxin has an apparent sulfur to iron ratio of 0.98
-
-
?
11-deoxycorticosterone + reduced adrenodoxin + O2
15beta-hydroxy-11-deoxycorticosterone + oxidized adrenodoxin + H2O
-
-
-
-
?
11-deoxycorticosterone + reduced adrenodoxin + O2
15beta-hydroxy-11-deoxycorticosterone + oxidized adrenodoxin + H2O
adrenodoxin is a [2Fe-2S] ferredoxin involved in electron transfer from NADPH+ (via a reductase) to cytochrome P-450 in the adrenal gland, 15beta-hydroxy-deoxycorticosterone is the only product that is observed, both in the case of wild-type CYP106A2 and all the mutants (except T396R)
-
-
?
11-deoxycorticosterone + reduced adrenodoxin + O2
15beta-hydroxy-11-deoxycorticosterone + oxidized adrenodoxin + H2O
deoxycorticosterone binds in the heme pocket near the iron ligand
-
-
?
11-oxo-beta-boswellic acid + reduced ferredoxin + O2
(3alpha,15beta)-3,15-dihydroxy-11-oxours-12-en-24-oic acid + H2O
-
a pentacyclic triterpene, 15beta-hydroxylation
-
-
?
11-oxo-beta-boswellic acid + reduced ferredoxin + O2
(3alpha,15beta)-3,15-dihydroxy-11-oxours-12-en-24-oic acid + H2O
Priestia megaterium ATCC 13368
-
a pentacyclic triterpene, 15beta-hydroxylation
-
-
?
abietic acid + reduced ferredoxin + O2
?
-
a pentacyclic triterpene
-
-
?
abietic acid + reduced ferredoxin + O2
?
Priestia megaterium ATCC 13368
-
a pentacyclic triterpene
-
-
?
progesterone + reduced adrenodoxin + O2
15beta-hydroxyprogesterone + oxidized adrenodoxin + H2O
adrenodoxin is a [2Fe-2S] ferredoxin involved in electron transfer from NADPH+ (via a reductase) to cytochrome P-450 in the adrenal gland
-
-
?
progesterone + reduced adrenodoxin + O2
15beta-hydroxyprogesterone + oxidized adrenodoxin + H2O
identification of monohydroxy progesterones using comparative HPLC and electrospray ionisation collision-induced dissociation mass spectrometry. 15beta-Hydroxy-progesterone is the main product. 6beta-Hydroxyprogesterone, 11alpha-hydroxyprogesterone, and 9alpha-hydroxyprogesterone are formed at small amounts
-
-
?
progesterone + reduced megaredoxin + O2
15beta-hydroxyprogesterone + oxidized megaredoxin + H2O
-
-
-
?
progesterone + reduced megaredoxin + O2
15beta-hydroxyprogesterone + oxidized megaredoxin + H2O
-
megaredoxin is an iron-sulfur protein of Bacillus megaterium, megaredoxin has an apparent sulfur to iron ratio of 0.98
-
-
?
additional information
?
-
-
hydroxylates a variety of 3-oxo-DELTA4-steroids in position 15beta in the presence of NADPH and O2. Ring A-reduced, aromatic, and 3beta-hydroxy-DELTA4-steroids do not serve as substrates
-
-
?
additional information
?
-
the specificity of hydroxylation in beta-position can be altered by the choice of the electron transfer system. Replacing the natural electron transfer partners by peroxides, the ratio of 15alpha-/15beta-hydroxylation of progesterone is increased 1.3fold
-
-
?
additional information
?
-
CYP106A2 catalyzes hydroxylations of a variety of 3-oxo-D4-steroids such as progesterone and deoxycorticosterone, mainly in the 15beta-position. The diterpene resin acid abietic acid is a substrate, that is converted to 12alpha- and 12beta-hydroxyabietic acid, catalytic site binding structure, homology modelling, overview
-
-
?
additional information
?
-
high-throughput substrate screening and binding affinities, substrate docking, overview
-
-
?
additional information
?
-
-
CYP106A2 from hydroxylates a variety of 3-oxo-DELTA4 steroids and catalyzes a one-step regioselective allylic hydroxylation of the diterpene abietic acid
-
-
?
additional information
?
-
-
enzyme reaction is coupled to NADPH oxidation, overview
-
-
?
additional information
?
-
-
enzyme produces hydroxylated metabolites at positions 6beta, 7beta, 9alpha, and 15beta and shows additionally 11-oxidase activity. No substrates: beta-estradiol, estrone, adrenosterone, and 19-hydroxyandrostenedione
-
-
?
additional information
?
-
enzyme produces hydroxylated metabolites at positions 6beta, 7beta, 9alpha, and 15beta and shows additionally 11-oxidase activity. No substrates: beta-estradiol, estrone, adrenosterone, and 19-hydroxyandrostenedione
-
-
?
additional information
?
-
-
enzyme produces hydroxylated metabolites at positions 6beta, 7beta, 9alpha,and 15beta and shows additionally 11-oxidase activity. No substrates: beta-estradiol, estrone, adrenosterone, and 19-hydroxyandrostenedione
-
-
?
additional information
?
-
enzyme produces hydroxylated metabolites at positions 6beta, 7beta, 9alpha,and 15beta and shows additionally 11-oxidase activity. No substrates: beta-estradiol, estrone, adrenosterone, and 19-hydroxyandrostenedione
-
-
?
additional information
?
-
the 3-oxo-DELTA4 moiety is not crucial for steroid conversion with CYP106A2. No substrates: estrone, estradiol, stigmasterol, and cholesterol
-
-
?
additional information
?
-
Priestia megaterium ATCC 13368
-
CYP106A2 from hydroxylates a variety of 3-oxo-DELTA4 steroids and catalyzes a one-step regioselective allylic hydroxylation of the diterpene abietic acid
-
-
?
additional information
?
-
Priestia megaterium ATCC 13368
CYP106A2 catalyzes hydroxylations of a variety of 3-oxo-D4-steroids such as progesterone and deoxycorticosterone, mainly in the 15beta-position. The diterpene resin acid abietic acid is a substrate, that is converted to 12alpha- and 12beta-hydroxyabietic acid, catalytic site binding structure, homology modelling, overview
-
-
?
additional information
?
-
Priestia megaterium ATCC 13368
high-throughput substrate screening and binding affinities, substrate docking, overview
-
-
?
