Taxadiene

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Taxadiene
Taxadiene.svg
Names
Systematic IUPAC name
Taxa-4,11-diene
Identifiers
3D model (JSmol)
ChemSpider
Properties
C20H32
Molar mass 272.476 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Taxadiene (taxa-4,11-diene) is a diterpene. Taxadiene is the first committed intermediate in the synthesis of taxol.[1] Six hydroxylation reactions, and a few others, are needed to convert taxadiene to baccatin III.

Enzymatically, taxadiene is produced from geranylgeranyl pyrophosphate by taxadiene synthase. A biochemical gram-scale production of taxadiene has been reported in 2010 using genetically engineered Escherichia coli.[2]

References[edit]

  1. ^ Lin, Xiaoyan; Hezari, Mehri; Koepp, Alfred E.; Floss, Heinz G.; Croteau, Rodney (1996). "Mechanism of Taxadiene Synthase, a Diterpene Cyclase That Catalyzes the First Step of Taxol Biosynthesis in Pacific Yew†". Biochemistry. 35 (9): 2968–77. doi:10.1021/bi9526239. PMID 8608134.
  2. ^ Ajikumar PK, Xiao WH, Tyo KE, Wang Y, Simeon F, Leonard E, et al. (2010). "Isoprenoid pathway optimization for Taxol precursor overproduction in Escherichia coli" (PDF). Science. 330 (6000): 70–4. doi:10.1126/science.1191652. PMC 3034138. PMID 20929806.