lecture890708 - Workspace
lecture890708 - Workspace
lecture890708 - Workspace
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Lanosterol → Cholesterol – Oxidative Demethylation<br />
• Several steps are required for conversion of lanosterol to cholesterol:<br />
HO<br />
1<br />
4<br />
H<br />
5<br />
24<br />
8<br />
H<br />
5<br />
14<br />
H<br />
lanosterol<br />
8<br />
1) Δ 24 hydrogenation<br />
2) 14α DEMETHYLATION<br />
3) 4α & 4β DEMETHYLATION<br />
4) Δ 8 to Δ 5 rearrangement<br />
1) Δ 24 hydrogenation 2) 14α DEMETHYLATION<br />
NADPH<br />
24<br />
NADP<br />
3) 4α & 4β DEMETHYLATION<br />
HO<br />
4) Δ 8 to Δ 5 rearrangement<br />
4<br />
H<br />
4x O 2<br />
4x H 2O<br />
P 450<br />
O<br />
H<br />
O O<br />
isomerase<br />
CO 2<br />
H<br />
14<br />
H<br />
O<br />
H<br />
H<br />
NAD<br />
NADH<br />
HO<br />
H<br />
H<br />
H<br />
H<br />
[-> vitamin D]<br />
H<br />
4x O 2<br />
4x H 2O<br />
cholesterol<br />
2x O2 P450 H O2 P450 H<br />
H<br />
2x H 2O<br />
O<br />
O<br />
H<br />
HO<br />
=<br />
P 450<br />
NADH<br />
NAD<br />
O<br />
HO<br />
H :BEnz<br />
O<br />
O III<br />
Fe<br />
H<br />
O O<br />
HCO 2H<br />
H<br />
CO 2<br />
O<br />
flat, rigid structure<br />
H<br />
NADPH<br />
NADP<br />
NADPH<br />
H<br />
HO<br />
H<br />
NADP<br />
H<br />
H
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