Taxadiene

Taxadiene

Names
Systematic IUPAC name Taxa-4,11-diene
Identifiers
ChemSpider	391697
Jmol interactive 3D	Image
PubChem	443484
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
SMILES C\1(=C2/CC[C@]3(C)CC/C=C(/C)[C@H]3C[C@H](CC/1)C2(C)C)C
Properties
Chemical formula	C20H32
Molar mass	272.48 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

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