Results 111 to 120 of about 1,120 (154)

Unraveling the Catalytic Mechanism of Taxadiene-5α-hydroxylase from Crystallography and Computational Analyses

ACS Catalysis
Paclitaxel is a famous chemotherapeutic agent, but its microbial production poses a long-standing challenge due to its poor product selectivity. Taxadiene-5α-hydroxylase (CYP725A4) plays a crucial role in the biosynthesis of paclitaxel, catalyzing the ...
Binju Wang, Huifeng Jiang, Zhenzhan Chang   +2 more
exaly   +3 more sources

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Natural and engineered production of taxadiene with taxadiene synthase

Biotechnology and Bioengineering, 2014
ABSTRACTTaxadiene synthase (TXS) is the rate‐limiting enzyme in the biosynthesis of paclitaxel, an important anticancer compound. TXS catalyzes the conversion of the diterpene precursor geranylgeranyl pyrophosphate (GGPP) into the diterpene taxadiene. Due to the importance of taxadiene in the overall biosynthetic pathway of paclitaxel biosynthesis, the
Sameh, Soliman, Yi, Tang
openaire   +2 more sources

A Promiscuous Proton in Taxadiene Biosynthesis?

Organic Letters, 2007
Herein we describe quantum chemical calculations on a two-step proton-transfer pathway that interconverts key intermediates in the biosynthesis of taxa-4,11-diene, a precursor of Taxol, that provides an energetically more favorable alternative to the usually proposed direct proton-transfer pathway. In effect, the bicyclic diterpene skeleton involved in
Pradeep, Gutta, Dean J, Tantillo
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The Taxadiene-Forming Carbocation Cascade

Journal of the American Chemical Society, 2011
A complete pathway (structures and energies of intermediates and transition state structures connecting them) from geranylgeranyl diphosphate to taxadiene, obtained using quantum chemical calculations, is described. This pathway is fully consistent with previous labeling experiments, despite differing in several subtle ways (in terms of conformations ...
Young J, Hong, Dean J, Tantillo
openaire   +2 more sources

Biosynthesis of Phomactins: Common Intermediate Phomactatriene and Taxadiene.

ChemInform, 2004
The stereochemical course of GGDP cyclization in the biosynthesis of phomactins is proposed by the stereochemistry of a cyclization product, phomacta-1(14),3,7-triene, isolated from Phomasp. and the results of incorporation experiments with [1-13C]- and [1,2-13C2]acetates.
Tetsuo, Tokiwano, Eri, Fukushi, Taeko, Endo, Hideaki, Oikawa   +3 more
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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, Howard J Williams, Charles A Roessner, A.Ian Scott   +3 more
openaire   +1 more source

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, Jia Wang, Yi Shi, Nan Wu, Xia Li, Ying Wang, Bingzhi Li, Wenhai Xiao, Mingdong Yao, Yingjin Yuan   +9 more
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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, Taeko, Endo, Tae, Tsukagoshi, Hitoshi, Goto, Eri, Fukushi, Hideaki, Oikawa   +5 more
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Biotransformation of a 4(20),11(12)-taxadiene derivative

Bioorganic & Medicinal Chemistry, 2001
A 4(20),11(12)-taxadiene derivative was converted to hydroxylated derivatives by Cunninghamella elegans AS3.2033 and Cunninghamella elegans var chibaensis ATCC 20230. Both microorganisms led to C-1 hydroxylations and conversion to a C-15-hydroxylated abeo-taxane.
D A, Sun, F, Sauriol, O, Mamer, L O, Zamir   +3 more
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Combined biotransformations of 4(20),11-taxadienes

Tetrahedron, 2005
Abstract Taxuyunnanine C ( 1 ) and its analogs ( 2 and 3 ), the C-14 oxygenated 4(20), 11-taxadienes from callus cultures of Taxus sp., were regio- and stereo-selectively hydroxylated at the 7β position by a fungus, Abisidia coerulea IFO 4011, and it was interesting that the longer the alkyl chain of the acyloxyl group at C-14 became, the
Jungui Dai, Lin Yang, Jun-ichi Sakai, Masayoshi Ando   +3 more
openaire   +1 more source