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Information on EC 1.14.15.6 - cholesterol monooxygenase (side-chain-cleaving)

for references in articles please use BRENDA:EC1.14.15.6

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IUBMB Comments

A heme-thiolate protein (cytochrome P-450). The reaction proceeds in three stages, with two hydroxylations at C-22 and C-20 preceding scission of the side-chain between carbons 20 and 22. The initial source of the electrons is NADPH, which transfers the electrons to the adrenodoxin via EC 1.18.1.6, adrenodoxin-NADP+ reductase.

The enzyme appears in viruses and cellular organisms
Reaction Schemes
hide(Overall reactions are displayed. Show all >>)
+
6
reduced adrenodoxin
+
3
+
6
=
+
+
6
oxidized adrenodoxin
+
4

Synonyms
p450scc, cyp11a1, cytochrome p-450scc, cytochrome p450scc, cyp11a, cholesterol side-chain cleavage enzyme, p450(scc), cholesterol side chain cleavage enzyme, cholesterol side-chain cleavage cytochrome p450, cytochrome p450 cholesterol side-chain cleavage, more

REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(20R,22R)-20,22-dihydroxy-cholesterol + 2 reduced adrenodoxin + O2 + 2 H+ = pregnenolone + 4-methylpentanal + 2 oxidized adrenodoxin + 2 H2O
show the reaction diagram
(1c)
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-
(22R)-22-hydroxycholesterol + 2 reduced adrenodoxin + O2 + 2 H+ = (20R,22R)-20,22-dihydroxycholesterol + 2 oxidized adrenodoxin + H2O
show the reaction diagram
(1b)
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-
-
cholesterol + 2 reduced adrenodoxin + O2 + 2 H+ = (22R)-22-hydroxycholesterol + 2 oxidized adrenodoxin + H2O
show the reaction diagram
(1a)
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-
-
cholesterol + 6 reduced adrenodoxin + 3 O2 + 6 H+ = pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
show the reaction diagram
overall reaction
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