New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method

Ojima, Iwao; Habuš, Ivan; Zhao, Mangzhu; Zucco, Martine; Park, Young Hoon; Sun, Ching Cherng; Brigaud, Thierry

doi:10.1016/s0040-4020(01)91210-4

Cited by 307 publications

(154 citation statements)

References 42 publications

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“…9-Dihydrotaxanes (7)(8)(9)(10)(11)(12)(13)(14) Taxus canadensis is the only species accumulating 9-dihydro-13-acetylbaccatin I11 (7, Fig. 1) in its needles in quantities 3-5 times that of taxol.…”

Section: A 9-keto-taxanesmentioning

confidence: 99%

“…The taxane 12 was described in a Chinese publication (14) and compound 13 was also found in Austrotaxus spicata (15). The derivatives [8][9][10][11] have not been found in other taxus species. We can subdivide this group of 9-dihydrotaxanes into those with an oxetane ring (7-11, Fig.…”

Section: A 9-keto-taxanesmentioning

confidence: 99%

“…Another very important drug, taxotere (which seems to be more active than taxol) (3, was derived by semisynthesis: the natural product 10-deacetyl baccatin I11 (which is abundant in Taxus baccata (6,7) and is very similar to the diterpenoid core of taxol) was chemically coupled at C-13 with a synthetic side chain. There are many reported syntheses of the side chain of taxol (8) and various derivatives are being made and tested.…”

Section: Introductionmentioning

confidence: 99%

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Taxus canadensis taxanes: structures and stereochemistry

Zamir¹,

Nedea²,

Zhou³

et al. 1995

Can. J. Chem.

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Abstract:The structures and stereochemistry of 14 taxanes isolated from Taxus cunadensis have been rigorously established by high-resolution NMR techniques and mass spectrometry. Taus canadensis is the only yew that accumulates 9-dihydro-13-acetylbaccatin 111 (also called 7,9-deacetylbaccatin VI) as the most abundant taxane. Five 9-dihydrotaxanes derived from the Canadian yew are novel natural products not reported in the needles of other species of yew (8-11, 14, Fig. 1).

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Section: A 9-keto-taxanesmentioning

confidence: 99%

Section: A 9-keto-taxanesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Taxus canadensis taxanes: structures and stereochemistry

Zamir¹,

Nedea²,

Zhou³

et al. 1995

Can. J. Chem.

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“…2), a naturally occurring biosynthetic precursor of Taxol, as the principal means of producing the drug to meet increasing demand (8)(9)(10). This semisynthetic method, however, involves several steps, including silyl protection and acetylation of 10-deacetylbaccatin III to afford 7-O-protected baccatin III, synthetic attachment of the N-Bz phenylisoserine side chain at the C-13 hydroxyl, and, finally, deprotection to yield Taxol (see Fig.…”

mentioning

confidence: 99%

Molecular cloning and heterologous expression of the C-13 phenylpropanoid side chain-CoA acyltransferase that functions in Taxol biosynthesis

Walker

Fujisaki

Long

et al. 2002

Proc. Natl. Acad. Sci. U.S.A.

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“…Of these, although total synthesis of taxol has been accomplished, commercial scale production of taxol from scratch using the available chemical methodologies is laborious and cost prohibitive strategy (Nicolaou et al, 1994). Taxol is manufactured using a semi-synthetic methodology, in which the side-chain section of the molecule is chemically synthesized and added to a plentiful metabolite of the needle of taxus species, 10-deacetyl baccatin en route to the taxol (Ojima et al, 1992). The other promising method is the plant cell culture and induction of the pathway with inducer such as methyl jasmonate and other regulators (Khosroushahi et al, 2006).…”

Section: Introductionmentioning

confidence: 99%

Cloning of taxadiene synthase gene into Arabidopsis thaliana (ecotype Columbia-0)

Choresca¹,

Gomez²,

Shin³

et al. 2010

Afr. J. Biotechnol.

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Paclitaxel (Taxol), a complex diterpenoid, produced by yew tree (Taxus sp.) is the most important chemotherapeutic agent that is widely used against a variety of malignancies such as ovarian and breast cancers. However, destructive methods for its production from natural resources together with currently used low-yielding industrial production systems via total synthesis or semi-synthesis have led researchers to invent a robust alternative biological production system using biotechnological approaches. The first committed step in taxol biosynthesis pathway is the production of taxadiene from geranylgeranyl diphosphate (GGPP) catalyzed by the plastid-localized enzyme taxadiene synthase (TXS). In this research, an attempt was made to evaluate the effects of the first critical enzyme in the taxol biosynthesis pathway on Arabidopsis plant through the expression of taxadiene synthase gene under the control of a dexamethasone-inducible promoter. To achieve this goal, Arabidopsis plants (ecotype Columbia-0) were transformed with the construct pTA-TXS-His via floral dip method using Agrobacterium tumefaciens AGL1. The transformed plants were confirmed using the PCR reaction amplifying an 800 bp fragment of the cloned gene. Upon these findings, a proposal was made that biotechnological strategies could be utilized for the production of taxol components.

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New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method

Cited by 307 publications

References 42 publications

Taxus canadensis taxanes: structures and stereochemistry

Taxus canadensis taxanes: structures and stereochemistry

Molecular cloning and heterologous expression of the C-13 phenylpropanoid side chain-CoA acyltransferase that functions in Taxol biosynthesis

Cloning of taxadiene synthase gene into Arabidopsis thaliana (ecotype Columbia-0)

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