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	163863-75-0;
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

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 8608134.2968-77&rft.date=1996&rft_id=info:doi/10.1021/bi9526239&rft_id=info:pmid/8608134&rft.aulast=Lin&rft.aufirst=Xiaoyan&rft.au=Hezari, Mehri&rft.au=Koepp, Alfred E.&rft.au=Floss, Heinz G.&rft.au=Croteau, Rodney&rfr_id=info:sid/en.wikipedia.org:Taxadiene" class="Z3988">
^ 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 20929806.70-4&rft.date=2010&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3034138#id-name=PMC&rft_id=info:pmid/20929806&rft_id=info:doi/10.1126/science.1191652&rft_id=info:bibcode/2010Sci...330...70A&rft.aulast=Ajikumar&rft.aufirst=PK&rft.au=Xiao, WH&rft.au=Tyo, KE&rft.au=Wang, Y&rft.au=Simeon, F&rft.au=Leonard, E&rft_id=http://dspace.mit.edu/bitstream/1721.1/81256/1/Stephanopoulos_Isoprenoid%20pathway.pdf&rfr_id=info:sid/en.wikipedia.org:Taxadiene" class="Z3988">

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[Xiaoyan-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 8608134.2968-77&rft.date=1996&rft_id=info:doi/10.1021/bi9526239&rft_id=info:pmid/8608134&rft.aulast=Lin&rft.aufirst=Xiaoyan&rft.au=Hezari, Mehri&rft.au=Koepp, Alfred E.&rft.au=Floss, Heinz G.&rft.au=Croteau, Rodney&rfr_id=info:sid/en.wikipedia.org:Taxadiene" class="Z3988">

[pmid20929806-2] 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. Bibcode:2010Sci...330...70A. doi:10.1126/science.1191652. PMC 3034138. PMID 20929806.70-4&rft.date=2010&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3034138#id-name=PMC&rft_id=info:pmid/20929806&rft_id=info:doi/10.1126/science.1191652&rft_id=info:bibcode/2010Sci...330...70A&rft.aulast=Ajikumar&rft.aufirst=PK&rft.au=Xiao, WH&rft.au=Tyo, KE&rft.au=Wang, Y&rft.au=Simeon, F&rft.au=Leonard, E&rft_id=http://dspace.mit.edu/bitstream/1721.1/81256/1/Stephanopoulos_Isoprenoid%20pathway.pdf&rfr_id=info:sid/en.wikipedia.org:Taxadiene" class="Z3988">

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