lecture890708 - Workspace
lecture890708 - Workspace
lecture890708 - Workspace
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Apparently Irregular Monoterpenes<br />
• Apparently irregular monoterpenes can also occur by non-cationic cyclisation of geranyl PP<br />
derivatives followed by extensive rearrangement<br />
– e.g. iridoids – named after Iridomyrmex ants but generally of plant origin and invariably glucosidated<br />
• e.g. seco-loganin (recall indole alkaloids) is a key component of strictosidine - precorsor to numerous complex<br />
medicinally important alkaloids:<br />
tryptophan<br />
isoprene<br />
geranyl PP<br />
N<br />
H H<br />
H<br />
MeO 2C<br />
NH<br />
OPP OPP<br />
O<br />
strictosidine<br />
[O]<br />
P 450<br />
H<br />
OGlu<br />
10<br />
NH 2<br />
N<br />
H<br />
tryptamine<br />
H 2O<br />
enzymatic<br />
Pictet-Spengler<br />
reaction<br />
OH<br />
H<br />
MeO2C H 2O<br />
2x NADP<br />
2x NADPH<br />
O<br />
PP i<br />
secologanin<br />
H<br />
O<br />
OGlu<br />
H<br />
O<br />
O<br />
10<br />
10-oxo geranal<br />
NADPH<br />
NADP<br />
O<br />
OH<br />
unusual reductive ring-closure -> cyclopentane<br />
(NB. Non-cationic)<br />
unusual fragmentation<br />
[O] P 450<br />
=<br />
OH<br />
O<br />
HO 2C<br />
H2O HO<br />
MeO2C O<br />
OP<br />
OGlu<br />
ATP<br />
ADP<br />
HO<br />
H<br />
MeO2C H<br />
[O] P450 H<br />
OGlu<br />
methylation<br />
O<br />
SAM<br />
HO2C loganin<br />
O<br />
[O]<br />
P 450<br />
O<br />
OH<br />
OH<br />
glycoside<br />
formation<br />
O<br />
OGlu
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