Taxadiene

Taxadiene
Names

IUPAC name Taxa-4,11-diene
Systematic IUPAC name (4aS,6S,12aS)-4,9,12a-Trimethyl-1,2,4a,5,6,7,8,11,12,12a-decahydro-6,10-methanobenzo[10]annulene
Identifiers
CAS Number	163594-75-0
3D model (JSmol)	Interactive image
ChemSpider	391697
PubChem CID	443484
CompTox Dashboard (EPA)	DTXSID40167621
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	272.476 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

Chemical compound

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" (PDF). Science. 330 (6000): 70–4. Bibcode:2010Sci...330...70A. doi:10.1126/science.1191652. PMC 3034138. PMID 20929806.