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Taxadiene information


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 Edit this at Wikidata
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]

  1. ^ Cite error: The named reference Xiaoyan was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference pmid20929806 was invoked but never defined (see the help page).

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Taxadiene

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Taxadiene (taxa-4,11-diene) is a diterpene. Taxadiene is the first committed intermediate in the synthesis of taxol. Six hydroxylation reactions, and...

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Diterpene

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important compounds such as retinol, phytol or taxadiene. Taxanes are class of diterpenoids featuring a taxadiene core. They are produced by plants of the genus...

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Taxadiene synthase

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The enzyme taxadiene synthase (EC 4.2.3.17) catalyzes the chemical reaction geranylgeranyl diphosphate ⇌ {\displaystyle \rightleftharpoons } taxa-4,11-diene...

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Taxane

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originally identified from plants of the genus Taxus (yews), and feature a taxadiene core. Paclitaxel (Taxol) and docetaxel (Taxotere) are widely used as chemotherapy...

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Paclitaxel

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intermediate known as taxadiene. Taxadiene then undergoes a series of 10 oxidations via NADPH, forming the intermediate taxadiene-5α-acetoxy-10β-ol (multiple...

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Terpene

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is a monoterpenoid, a tropolone derivative. Humulene, a sesquiterpene. Taxadiene, a diterpene, precursor to the diterpenoid taxol, an anticancer agent...

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Taxadienone

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reported in 2012 together with its conversion to the next Taxol precursor taxadiene. A multigram synthetic method was reported in 2015. GEN News Highlights...

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Alkene

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compounds in nature Limonene, a monoterpene. Humulene, a sesquiterpene. Taxadiene, a diterpene, precursor to the diterpenoid taxol, an anticancer agent...

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C20H32

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diterpene Sclarene, a diterpene Stemarene, a diterpene Stemodene, a diterpene Taxadiene, a taxane diterpene This set index page lists chemical structure articles...

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Taxine alkaloids

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show whether taxine B could also be used as a pharmaceutical. Taxane Taxadiene Omacetaxine Graf, Engelbert; Kirfel, Armin; Wolff, Gerd-Joachim; Breitmaier...

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Baccatin III

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same accomplishment with Escherichia coli in 2000. 10-Deacetylbaccatin Taxadiene Han F, Kang LZ, Zeng XL, Ye ZW, Guo LQ, Lin JF (2014). "Bioproduction...

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Taxusin

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isolate derived from Taxus wallichiana. Taxusin can be used to synthesize taxadiene -diol and -triol derivatives via deoxygenation. Taxoid 7beta-hydroxylase...

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Paclitaxel total synthesis

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C1–C2 bond. Ongoing research efforts are directed at the synthesis of taxadiene and taxadienone intermediates. The synthesis of related taxanes decinnamoyltaxinine...

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Terpene synthase C terminal domain

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includes copalyl diphosphate synthase (kaurene synthase A). Tpsd includes taxadiene synthase, pinene synthase, and myrcene synthase. Tpse includes ent-kaurene...

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Terpene synthase N terminal domain

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includes copalyl diphosphate synthase (kaurene synthase A). Tpsd includes taxadiene synthase, pinene synthase, and myrcene synthase. Tpse includes ent-kaurene...

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Juvabione

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FPP precursor. Examples include: Myrcene synthase, pinene synthase, and taxadiene synthase Manville, J. F.; Kriz, C. D. (1977). "Juvabione and its analogues...

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Index of molecular biology articles

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- taq polymerase - TATA box - taurochenodeoxycholate 6α-hydroxylase - taxadiene 5alpha-hydroxylase - taxane 10beta-hydroxylase - TAZ zinc finger - Tbf5...

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