Taxadiene

Taxadiene
Names

Systematic IUPAC name Taxa-4,11-diene
Identifiers
ChemSpider	391697
InChI InChI=1S/C20H32/c1-14-7-6-11-20(5)12-10-17-15(2)8-9-16(13-18(14)20)19(17,3)4/h7,16,18H,6,8-13H2,1-5H3/t16-,18+,20-/m0/s1 Key: FRJSECSOXKQMOD-HQRMLTQVSA-N InChI=1/C20H32/c1-14-7-6-11-20(5)12-10-17-15(2)8-9-16(13-18(14)20)19(17,3)4/h7,16,18H,6,8-13H2,1-5H3/t16-,18+,20-/m0/s1 Key: FRJSECSOXKQMOD-HQRMLTQVBK
Jmol-3D images	Image
PubChem	443484
SMILES C\1(=C2/CC[C@]3(C)CC/C=C(/C)[C@H]3C[C@H](CC/1)C2(C)C)C
Properties
Molecular formula	C₂₀H₃₂
Molar mass	272.47 g·mol⁻¹
Except where noted otherwise, data is 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

↑ 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.
↑ 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.". Science 330 (6000): 70–4. doi:10.1126/science.1191652. PMC 3034138. PMID 20929806.