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Literature summary for 1.14.14.19 extracted from

  • Akhtar, M.; Wright, J.N.; Lee-Robichaud, P.
    A review of mechanistic studies on aromatase (CYP19) and 17alpha-hydroxylase-17,20-lyase (CYP17) (2010), J. Steroid Biochem. Mol. Biol., 125, 2-12.
    View publication on PubMed

Activating Compound

Activating Compound Comment Organism Structure
cytochrome b5 expression of cytochrome b5 in the zona reticularis, at the onset of adrenarche, increases along with the acyl-carbon bond cleavage activity of CYP17, cytochrome plays a regulatory role for CYP17 activity Homo sapiens

Protein Variants

Protein Variants Comment Organism
R347A site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5 Homo sapiens
R347H site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5 Homo sapiens
R358A site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5 Homo sapiens
R358Q site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5 Homo sapiens
R449A site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5 Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
19-azido-androstenedione
-
Homo sapiens
19-thiomethyl-androstenedione
-
Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Homo sapiens cytochrome P-450 17alpha-hydroxylase-17,20-lyase, CYP17, is a multifunctional enzyme. CYP17 catalyzes at the same active site not only the hydroxylation process but also an acyl-carbon bond cleavage reaction which involves the nucleophilic attack of the ferric-peroxyanion, Fe(III)-O-O-, on the acyl-carbon to furnish a tetrahedral intermediate which fragments, leading to acyl-carbon cleavage ?
-
?
pregnenolone + AH2 + O2 Homo sapiens
-
17alpha-hydroxypregnenolone + A + H2O
-
?
progesterone + AH2 + O2 Homo sapiens
-
17alpha-hydroxyprogesterone + A + H2O
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
zona reticularis a adrenal cortex tissue layer that excretes androgens Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information cytochrome P-450 17alpha-hydroxylase-17,20-lyase, CYP17, is a multifunctional enzyme. CYP17 catalyzes at the same active site not only the hydroxylation process but also an acyl-carbon bond cleavage reaction which involves the nucleophilic attack of the ferric-peroxyanion, Fe(III)-O-O-, on the acyl-carbon to furnish a tetrahedral intermediate which fragments, leading to acyl-carbon cleavage Homo sapiens ?
-
?
additional information for the formation of the 16,17-ene steroid, the Fe(III)-O-O- species is trapped by the progestogen, prior to hydroxylation, and the resulting peroxy adduct decomposes to generate a C-17 radical, which is neutralized by a disproportionation reaction involving the loss of C-16-hydrogen atom, mechanism of the acyl-carbon bond cleavage reactions catalysed by CYP17, pathways for the formation of three cleavage products from peroxy adducts, overview Homo sapiens ?
-
?
pregnenolone + AH2 + O2
-
Homo sapiens 17alpha-hydroxypregnenolone + A + H2O
-
?
progesterone + AH2 + O2
-
Homo sapiens 17alpha-hydroxyprogesterone + A + H2O
-
?

Synonyms

Synonyms Comment Organism
17alpha-hydroxylase-17,20-lyase
-
Homo sapiens
CYP17
-
Homo sapiens

General Information

General Information Comment Organism
additional information in the case of CYP17 the attack of Fe(III)-O-O(-) on the target carbon is promoted by cytochrome b5, which acts as a conformational regulator of CYP17. It is this regulation of CYP17 that provides a safety mechanism which ensures that during corticoid biosynthesis, which involves 17alpha-hydroxylation by CYP17, androgen formation is avoided Homo sapiens