KEGG   ENZYME: 1.14.14.197
Entry
EC 1.14.14.197              Enzyme                                 
Name
progesterone 11alpha-monooxygenase;
progesterone 11alpha-hydroxylase;
CYP509C12 (gene name);
CYP68L1 (gene name);
CYP68L8 (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
progesterone,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (11alpha-hydroxylating)
Reaction(IUBMB)
progesterone + [reduced NADPH---hemoprotein reductase] + O2 = 11alpha-hydroxyprogesterone + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R02214]
Reaction(KEGG)
R02214
Substrate
progesterone [CPD:C00410];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
11alpha-hydroxyprogesterone [CPD:C03747];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme-thiolate) enzyme. The enzyme, isolated from fungi, can hydroxylate testosterone, androst-4-ene-3,17-dione, and 11-deoxycorticosterone, forming the respective 11alpha-hydroxy compounds (cf. EC 1.14.15.4, steroid 11beta-monooxygenase). The CYP509C12 enzyme from Rhizopus arrhizus can also 6-hydroxylate testosterone and 11-deoxycorticosterone, forming the respective beta-hydroxy compounds [2].
History
EC 1.14.14.197 created 1972 as EC 1.14.99.14, transferred 2025 to EC 1.14.14.197
Reference
1  [PMID:5417182]
  Authors
Shibahara M, Moody JA, Smith LL.
  Title
Microbial hydroxylations. V. 11-alpha-hydroxylation of progesterone by cell-free preparations of Aspergillus ochraceus.
  Journal
Biochim Biophys Acta 202:172-9 (1970)
DOI:10.1016/0005-2760(70)90228-6
Reference
2  [PMID:20850485]
  Authors
Petric S, Hakki T, Bernhardt R, Zigon D, Cresnar B.
  Title
Discovery of a steroid 11alpha-hydroxylase from Rhizopus oryzae and its biotechnological application.
  Journal
J Biotechnol 150:428-37 (2010)
DOI:10.1016/j.jbiotec.2010.09.928
Reference
3  [PMID:39766209]
  Authors
Ortega-de Los Rios L, Getino L, Galan B, Garcia JL, Luengo JM, Chamizo-Ampudia A, Fernandez-Canon JM.
  Title
Unlocking Testosterone Production by Biotransformation: Engineering a Fungal Model of Aspergillus nidulans Strain Deficient in Steroid 11alpha-Hydroxylase Activity and Expressing 17beta-Hydroxysteroid Dehydrogenase Enzyme as Proof of Concept.
  Journal
Biomolecules 14:biom14121502 (2024)
DOI:10.3390/biom14121502
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.197
IUBMB Enzyme Nomenclature: 1.14.14.197
ExPASy - ENZYME nomenclature database: 1.14.14.197
BRENDA, the Enzyme Database: 1.14.14.197
CAS: 37256-77-2
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