lecture890708 - Workspace
lecture890708 - Workspace
lecture890708 - Workspace
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Diterpenes – Geranylgeranyl PP → Taxol<br />
• Taxol is a potent anti-cancer agent used in the treatment of breast & ovarian cancers<br />
– comes from the bark of the pacific yew (Taxus brevifolia)<br />
– binds to tubulin and intereferes with the assembly of microtubules<br />
• biosynthesis is from geranylgeranyl PP:<br />
OPP<br />
geranylgeranyl PP<br />
cyclisation<br />
14-exo<br />
– for details see: http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/terp/taxadiene.html<br />
– home page is: http://www.chem.qmul.ac.uk/iubmb/enzyme/<br />
OPP<br />
b<br />
H<br />
a<br />
H<br />
a<br />
b<br />
• recommendations of the Nomenclature Committee of the International Union of Biochemistry and Molecular Biology on the<br />
Nomenclature and Classification of Enzyme-Catalysed Reactions<br />
• based at Department of Chemistry, Queen Mary University of London<br />
BzNH<br />
HO<br />
Ph<br />
β-amino acid<br />
(shikimate)<br />
O<br />
O<br />
AcO<br />
HO<br />
BzO AcO<br />
cembrene<br />
O<br />
H<br />
OH<br />
O<br />
taxol<br />
sesquiterpene<br />
(isoprenoid)
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