lecture890708 - Workspace
lecture890708 - Workspace
lecture890708 - Workspace
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Monoterpenes – α-Terpinyl Cation Formation<br />
• geranyl pyrophosphate isomerises readily via an allylic cation to linalyl & neryl pyrophosphates<br />
– the leaving group abilty of pyrophosphate is enhanced by coordination to 3 × Mg 2+<br />
– all three pyrophosphates are substrates for cyclases via an α-terpinyl cation:<br />
OPP<br />
(E)<br />
OPP<br />
(Z)<br />
gerenyl<br />
pyrophosphate<br />
linalyl<br />
pyrophosphate<br />
OPP<br />
neryl<br />
pyrophosphate<br />
allylic cation<br />
intimate ion pair<br />
O<br />
O<br />
P O O<br />
Mg<br />
P O<br />
O<br />
O<br />
cyclase<br />
Mg<br />
initial<br />
chiral centre<br />
OPP<br />
=<br />
α-terpinyl cation<br />
OPP<br />
MONOTERPENES (C 10)
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