lecture890708 - Workspace
lecture890708 - Workspace
lecture890708 - Workspace
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Aristolochene & 5-Epi-Aristolochene Synthases<br />
• molecular modelling studies indicate that the shape of the active sites determines the conformation<br />
of FPP and thus the stereochemistry of the final product<br />
– Penicillium roqueforti aristolochene synthase – Felicetti & Cane J. Am. Chem. Soc. 2004, 126, 7212 (DOI)<br />
PPO<br />
10-exo<br />
Phe-112<br />
E,E-FPP<br />
PPO H<br />
Phe-112<br />
germacrene A<br />
(+)-aristolochene<br />
H<br />
H<br />
– tobacco 5-epi-aristolochene synthase – Starks, Back, Chappell & Noel Science 1997, 277, 1815 (DOI)<br />
PPO<br />
cyclisation<br />
elimination<br />
H<br />
E,E-FPP<br />
Tyr–O<br />
cyclisation<br />
10-exo<br />
elimination<br />
1,2-alkyl<br />
shift<br />
TyrOH<br />
held by enzyme active site in different conformations from above<br />
(R)<br />
H<br />
H<br />
(S)<br />
H<br />
cation<br />
formation<br />
1,2-hydride<br />
shift<br />
H<br />
H<br />
transannular<br />
cyclisation<br />
eudesmane cation<br />
germacrene 5-epi-aristolochene
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