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Characterization and Expression Profile Analysis of a New cDNA Encoding Taxadiene Synthase from Taxus media

open access: yesBMB Reports, 2005
A full-length cDNA encoding taxadiene synthase (designated as TmTXS), which catalyzes the first committed step in the Taxol biosynthetic pathway, was isolated from young leaves of Taxus media by rapid amplification of cDNA ends (RACE). The full-length cDNA of TmTXS had a 2586 bp open reading frame (ORF) encoding a protein of 862 amino acid residues ...
Lingxia Zhao, Guoyin Kai, Xiaofen Sun
exaly   +4 more sources
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Taxadiene Synthase-Catalyzed Cyclization of 6-Fluorogeranylgeranyl Diphosphate to 7-Fluoroverticillenes

Journal of the American Chemical Society, 2005
The mechanism of the taxadiene synthase-catalyzed cyclization of (E,E,E)-geranylgeranyl diphosphate (GGPP, 7) to taxadiene (5) is proposed to proceed through a verticillen-12-yl carbocation intermediate (8) that undergoes an 11 --> 7 proton transfer leading to formation of the C ring.
Yinghua Jin   +2 more
exaly   +3 more sources

Proposed mechanism for diterpene synthases in the formation of phomactatriene and taxadiene

Organic & Biomolecular Chemistry, 2005
To obtain insight into how the cyclization pathway is controlled, the mechanism of diterpene synthase reactions (the putative phomactatriene synthase and taxadiene synthases) involving the same intermediate was investigated in detail. The mechanism of the initial transformation of GGDP to verticillen-12-yl cation (A+) was proposed based on the ...
Tetsuo, Tokiwano   +5 more
openaire   +2 more sources

Studies on Taxadiene Synthase:  Interception of the Cyclization Cascade at the Isocembrene Stage with GGPP Analogues

Journal of Organic Chemistry, 2005
[reaction: see text] The cyclization of GGPP to taxadiene, catalyzed by taxadiene synthase, has been suggested to proceed through a series of monocyclic isocembrenyl- and bicyclic verticillyl-carbocationic intermediary stages. A set of GGPP analogues with abolished or perturbed pi-nucleophilicity at the delta10 double bond (GGPP numbering) was ...
Samik Nanda
exaly   +3 more sources

Sesquiterpenes produced by truncated taxadiene synthase

Tetrahedron Letters, 2000
Abstract Soluble, highly active N-terminal truncated taxadiene synthase catalyzes the formation of an isomeric mixture of taxadienes from geranylgeranyl diphosphate. Farnesyl diphosphate was also found to be a good substrate, producing four sesquiterpenes which were characterized.
Qiulong Huang   +3 more
exaly   +2 more sources

Catalytic Control in the Facile Proton Transfer in Taxadiene Synthase

ACS Catalysis, 2017
Enzymes are highly efficient and usually very specific biocatalysts. However, some enzyme families, such as terpene synthases, are inherently promiscuous due to the extremely challenging chemistry they have evolved to tackle. Here we focus on one such enzyme, taxadiene synthase (TXS), which produces taxa-4(5),11(12)-diene, a key precursor to the ...
Yehoshua Freud   +2 more
openaire   +1 more source

Heterologous Expression and Characterization of a “Pseudomature” Form of Taxadiene Synthase Involved in Paclitaxel (Taxol) Biosynthesis and Evaluation of a Potential Intermediate and Inhibitors of the Multistep Diterpene Cyclization Reaction

Archives of Biochemistry and Biophysics, 2000
The diterpene cyclase taxadiene synthase from yew (Taxus) species transforms geranylgeranyl diphosphate to taxa-4(5),11(12)-diene as the first committed step in the biosynthesis of the anti-cancer drug Taxol. Taxadiene synthase is translated as a preprotein bearing an N-terminal targeting sequence for localization to and processing in the plastids ...
Mark R Wildung   +2 more
exaly   +3 more sources

Improving the expression of taxadiene synthase to enhance the titer of taxadiene in Saccharomyces cerevisiae

Green Chemistry
Improve the synthesis of taxadiene in Saccharomyces cerevisiae .
Chenglong Zhang   +9 more
openaire   +1 more source

Studies on taxadiene synthase: interception of the cyclization cascade at the verticillene stage and rearrangement to phomactatriene

Tetrahedron, 2007
Abstract The cyclization of geranylgeranyl diphosphate (GGDP) to taxadiene catalyzed by taxadiene synthase has been suggested to proceed in stages, involving a transient bicyclic verticillyl carbocation intermediate, which also has been proposed in the biosynthetic pathway leading to phomactatriene by marine fungi of Phoma sp.
Siew Yin Chow   +5 more
openaire   +1 more source

Mechanism of Taxadiene Synthase, a Diterpene Cyclase That Catalyzes the First Step of Taxol Biosynthesis in Pacific Yew

Biochemistry, 1996
The first committed step in the formation of taxol has been shown to involve the cyclization of geranylgeranyl diphosphate to taxa-4(5),11(12)-diene. The formation of this endocyclic diterpene olefin isomer as the precursor of taxol was unexpected, since the exocyclic isomer, taxa-4(20),11(12)-diene, had been predicted as the initial product of the ...
X, Lin   +4 more
openaire   +2 more sources

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