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Triterpenes – Squalene → 2,3-Oxidosqualene<br />

• squalene is oxidised to 2,3-oxidosqualene by squalene oxidase – which is an O 2/FADH 2dependent<br />

enzyme:<br />

• the key oxidant is a peroxyflavin:<br />

O<br />

O O<br />

HN<br />

FADH 2<br />

squalene<br />

H<br />

N O<br />

NR<br />

NH<br />

O<br />

O<br />

O<br />

HN<br />

H<br />

N O<br />

NR<br />

peroxyflavin<br />

NH<br />

squalene<br />

oxidase<br />

O 2 + FADH 2<br />

H 2O + FAD<br />

reductive recycling<br />

O<br />

O<br />

HO<br />

H N<br />

O<br />

H<br />

N O<br />

NR<br />

N<br />

hydroxyflavin<br />

H 2O<br />

2,3-oxidosqualene<br />

O<br />

N<br />

FAD<br />

H<br />

N O<br />

NR<br />

N

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