Taxadiene (taxa-4,11-diene) is a

diterpene Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being ...

. Taxadiene is the first committed intermediate in the synthesis of

taxol Paclitaxel (PTX), sold under the brand name Taxol among others, is a chemotherapy medication used to treat a number of types of cancer. This includes ovarian cancer, esophageal cancer, breast cancer, lung cancer, Kaposi's sarcoma, cervical cance ...

. Six hydroxylation reactions, and a few others, are needed to convert taxadiene to

baccatin III Baccatin III is an isolate from the yew tree (Genera ''Taxus''). Baccatin III is a precursor to the anti-cancer drug paclitaxel (Taxol). In 2014, researchers reported introduction and expression of the endophytic fungal gene responsible for synt ...

. Enzymatically, taxadiene is produced from

geranylgeranyl pyrophosphate Geranylgeranyl pyrophosphate is an intermediate in the biosynthesis of diterpenes and diterpenoids. It is also the precursor to carotenoids, gibberellins, tocopherols, and chlorophylls. It is also a precursor to geranylgeranylated proteins, whi ...

taxadiene synthase The enzyme taxadiene synthase (EC 4.2.3.17) catalyzes the chemical reaction :geranylgeranyl diphosphate \rightleftharpoons taxa-4,11-diene + diphosphate This enzyme belongs to the family of lyases, specifically those carbon-oxygen lyases actin ...

. A biochemical gram-scale production of taxadiene has been reported in 2010 using genetically engineered ''

Escherichia coli ''Escherichia coli'' (),Wells, J. C. (2000) Longman Pronunciation Dictionary. Harlow ngland Pearson Education Ltd. also known as ''E. coli'' (), is a Gram-negative, facultative anaerobic, rod-shaped, coliform bacterium of the genus ''Escher ...

''.

References

Dienes Taxanes Diterpenes {{organic-compound-stub