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学科主题: 药学
题名:
Regio- and stereo-selective biotransformation of 2 alpha,5 alpha,10 beta,14 beta-tetra-acetoxy-4(20), 11-taxadiene by Ginkgo cell suspension cultures
作者: Dai, JG; Ye, M; Guo, HZ; Zhu, WH; Zhang, DO; Hu, Q; Zheng, JH; Guo, D
关键词: taxane ; sinenxan A ; biotransformation ; enzymes ; cell suspension cultures ; Ginkgo biloba
刊名: TETRAHEDRON
发表日期: 2002-07-08
卷: 58, 期:28, 页:5659-5668
收录类别: IC ; SCI
文章类型: Article
WOS标题词: Science & Technology
类目[WOS]: Chemistry, Organic
研究领域[WOS]: Chemistry
关键词[WOS]: BIOLOGICAL EVALUATION ; MULTIDRUG-RESISTANCE ; TAXOL BIOSYNTHESIS ; PACIFIC YEW ; AGENT ; CYTOCHROME-P450 ; MECHANISM ; SYNTHASE ; ANALOGS ; TAXUS
英文摘要:

Ginkgo biloba cell suspension cultures were used to bioconvert sinenxan A, 2alpha,5alpha, 10beta, 14beta-tetra-acetoxy-4(20), 11-taxadiene, a taxoid isolated from callus tissue cultures of Taxus spp. Besides two major products, 9alpha-hydroxy-2alpha,5alpha,10beta,14beta-tetra-acetoxy-4(20), 11-taxadiene 1 and 9alpha,10beta-dihydroxy-2alpha,5alpha,14beta-triacetoxy-4(20), 11-taxadiene 2, additional six minor products were obtained and five of them identified as new compounds. On the basis of chemical and spectral data, their structures were identified as 9alpha,14beta-dihydroxy-2alpha,5alpha,10beta-triacetoxy-4(20), 11-taxadiene 3, 6alpha,10beta-dihydroxy-2alpha,5alpha,14beta-triacetoxy-4(20), 11-taxadiene 4, 6alpha,9alpha,10beta-trihydroxy-2alpha,5alpha,14beta-triacetoxy-4(20), 11-taxadiene 5, 9alpha,10beta-O-(propane-2,2-diyl)-2alpha,5alpha,14beta-triacetoxy-4(20), 11-taxadiene 6, 9alpha-hydroxy-2alpha,5alpha,10beta,14beta-tetra-acetoxy-4(20), 11-taxadiene formate 7, 10beta-hydroxy-2alpha,5alpha,9alpha,14beta-tetra-acetoxy-4(20), 11-taxadiene formate 8, respectively. Investigation of the properties of the enzymes responsible for the biocatalysis process of sinenxan A to I and 2 revealed that the enzymes were extracellular and constitutive. Using sinenxan A and the two major products (1 and 2) as indicators, the stage and concentration of sinenxan A added and the kinetics of the biotransformation reaction were investigated. The results showed that: (1) the optimal stage for sinenxan A addition was the logarithmic phase of the cell growth period, in which sinenxan A was almost completely bioconverted, and the biotransformation rates were up to 60 and 20% for 1 and 2, respectively; (2) the optimal concentration of sinenxan A added was 60 mg/L; (3) the substrate was mainly converted into 1 and 2 in the first 48 h after addition and then into the minor products. (C) 2002 Elsevier Science Ltd. All rights reserved.

语种: 英语
WOS记录号: WOS:000176697100011
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/60411
Appears in Collections:北京大学药学院_期刊论文

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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, Inst Mat Med, Beijing 100050, Peoples R China
3.Peking Union Med Coll, Beijing 100050, Peoples R China

Recommended Citation:
Dai, JG,Ye, M,Guo, HZ,et al. Regio- and stereo-selective biotransformation of 2 alpha,5 alpha,10 beta,14 beta-tetra-acetoxy-4(20), 11-taxadiene by Ginkgo cell suspension cultures[J]. TETRAHEDRON,2002,58(28):5659-5668.
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