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Information on EC 1.14.13.54 - ketosteroid monooxygenase

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IUBMB Comments
A single FAD-containing enzyme catalyses three types of monooxygenase (Baeyer-Villiger oxidation) reaction. The oxidative esterification of a number of derivatives of progesterone to produce the corresponding 17alpha-hydroxysteroid 17-acetate ester, such as testosterone acetate, is shown in Reaction (1). The oxidative lactonization of a number of derivatives of androstenedione to produce the 13,17-secoandrosteno-17,13alpha-lactone, such as testololactone, is shown in Reaction (2). The oxidative cleavage of the 17beta-side-chain of 17alpha-hydroxyprogesterone to produce androstenedione and acetate is shown in Reaction (3). Reaction (1) is also catalysed by EC 1.14.99.4 (progesterone monooxygenase), and Reactions (2) and (3) correspond to that catalysed by EC 1.14.99.12 (androst-4-ene-3,17-dione monooxygenase). The possibility that a single enzyme is responsible for the reactions ascribed to EC 1.14.99.4 and EC 1.14.99.12 in other tissues cannot be excluded.
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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
17alpha-Hydroxyprogesterone, NADPH2:oxygen oxidoreductase (20-hydroxylating, side-chain cleaving), Androgen hydroxylase, Androstenedione, NADPH2:oxygen oxidoreductase (17-hydroxylating, lactonizing), Baeyer-Villiger monooxygenase, BVMO, CYP106A2, Hydroxylase, steroid, NADPH-dependent steroid Baeyer-Villiger monooxygenase, Oxygenase, steroid mono-, Progesterone, NADPH2:oxygen oxidoreductase (20-hydroxylating, ester-producing), more
REACTION
REACTION DIAGRAM
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ORGANISM
UNIPROT
LITERATURE
17alpha-hydroxyprogesterone + NADPH + H+ + O2 = androstenedione + acetate + NADP+ + H2O
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(3)
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a ketosteroid + NADPH + H+ + O2 = a steroid ester/lactone + NADP+ + H2O
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androstenedione + NADPH + H+ + O2 = testololactone + NADP+ + H2O
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(2)
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progesterone + NADPH + H+ + O2 = testosterone acetate + NADP+ + H2O
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(1)
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