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Substrate specificity for the hydroxylation of polyoxygenated 4(20),11-taxadienes by Ginkgo cell suspension cultures
Dai, JG; Ye, M; Guo, HZ; Zhu, WH; Zhang, DY; Hu, Q; Zheng, JH; Guo, D
关键词taxane 4(20),11-taxadiene hydroxylation cell suspension cultures Ginkgo biloba L.
刊名BIOORGANIC CHEMISTRY
2003-08-01
DOI10.1016/S0045-2068(03)00063-4
31期:4页:345-356
收录类别SCI
文章类型Article
WOS标题词Science & Technology
类目[WOS]Biochemistry & Molecular Biology ; Chemistry, Organic
研究领域[WOS]Biochemistry & Molecular Biology ; Chemistry
关键词[WOS]1ST TOTAL-SYNTHESIS ; CUNNINGHAMELLA-ECHINULATA ; MULTIDRUG-RESISTANCE ; TAXOL ; TAXUS ; BIOTRANSFORMATION ; EFFICIENT ; CANCER ; AGENT ; RING
英文摘要

Three C-14 oxygenated taxanes isolated from callus cultures of Taxus spp., 2alpha,5alpha,10beta,14beta-tetra-acetoxy-4(20), 11-taxadiene 3, 2alpha,5alpha,10beta-triacetoxy-14beta-propionyloxy-4(20),11-taxadiene 4, 2alpha,5alpha,10beta-triacetoxy-14beta-(2-methylbutyryl)-oxy-4(20),I I-taxadiene 5, and three deacetylated derivatives of 3, 10beta-hydroxy-2alpha,5alpha,14beta-triacetoxy-4(20),11-taxadiene 6, 14beta-hydroxy-2alpha,5alpha, 10beta-triacetoxy-4(20),11-taxadiene 7, 10beta,14beta-dihydroxy-2alpha,5alpha-diacetoxy-4(20),11-taxadiene 8, could all be regio- and stereo-selectively hydroxylated at the 9alpha-position by Ginkgo cell suspension cultures to yield a series of new 9alpha,14beta-dihydroxylated taxoids. The effects of functional groups, especially at C-14 of the substrates, on the biotransformation were also investigated. The results revealed that substrates with an acetoxyl group at C-14 could be more efficiently 9alpha-hydroxylated than those with a longer ester chain or a hydroxyl group at C-14. An acetoxyl or hydroxyl group at C-10 had no effect on the conversion rates of the substrates, but substrates with the hydroxyl group (compared with the acetoxyl analogues) could be converted into 9alpha-hydroxylated products more easily. (C) 2003 Elsevier Science (USA). All rights reserved.

语种英语
WOS记录号WOS:000184507600007
引用统计
被引频次:8[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/63965
专题北京大学药学院
作者单位1.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China
2.Chinese Acad Med Sci & Peking Union Med Coll, Inst Mat Med, Beijing 100050, Peoples R China
推荐引用方式
GB/T 7714
Dai, JG,Ye, M,Guo, HZ,et al. Substrate specificity for the hydroxylation of polyoxygenated 4(20),11-taxadienes by Ginkgo cell suspension cultures[J]. BIOORGANIC CHEMISTRY,2003,31(4):345-356.
APA Dai, JG.,Ye, M.,Guo, HZ.,Zhu, WH.,Zhang, DY.,...&Guo, D.(2003).Substrate specificity for the hydroxylation of polyoxygenated 4(20),11-taxadienes by Ginkgo cell suspension cultures.BIOORGANIC CHEMISTRY,31(4),345-356.
MLA Dai, JG,et al."Substrate specificity for the hydroxylation of polyoxygenated 4(20),11-taxadienes by Ginkgo cell suspension cultures".BIOORGANIC CHEMISTRY 31.4(2003):345-356.
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