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题名: Regioselective acylation of nucleosides and their analogs catalyzed by Pseudomonas cepacia lipase: enzyme substrate recognition
作者: Li, Ning1, 2;  Zong, Min-Hua1;  Ma, Ding2
通讯作者: M. Zong ;  马丁
关键词: Floxuridine ;  Lipase ;  Nucleosides ;  Regioselective acylation ;  Substrate recognition
刊名: TETRAHEDRON
发表日期: 2009-01-31
DOI: 10.1016/j.tet.2008.11.045
卷: 65, 期:5, 页:1063-1068
收录类别: SCI ;  IC
文章类型: Article
部门归属: 5
项目归属: 502
产权排名: 2;1
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Organic
研究领域[WOS]: Chemistry
英文摘要: The substrate recognition of Pseudomonas cepacia lipase in the acylation of nucleosides was investigated by means of rational Substrate engineering for the first time. P. cepacia lipase displayed excellent 3'-regioselectivities (96 to >99%) in the lauroylation of 2'-deoxynucleosides la-le, while low to good 3'-regioselectivities (59-89%) in the lauroylation of ribonucleosides 1f-1j. It might be due to the unfavorable hydrogen bond interaction between 2'-hydroxyl group of 1f-1j and phenolic hydroxyl group of tyrosine residue present in the alternate hydrophobic pocket of the enzyme, which stabilizes the conformation of 5'-acylation transition state and thus increases the amount of the minor regioisomer. In addition, various ester derivatives of floxuridine were synthesized successfully by the lipase with high conversions (99%) and good to excellent 3'-regioselectivities under mild conditions. The recognition of various acyl donors by the enzyme was examined. The enzymatic recognition of acyl groups was rationalized in terms of the structure of the active site of the lipase, especially the size, shape, and physicochemical properties. (C) 2008 Elsevier Ltd. All rights reserved.
关键词[WOS]: ACID ESTER PRODRUGS ;  SOLUTION-PHASE SYNTHESIS ;  IONIC LIQUID ;  DERIVATIVES ;  FLOXURIDINE ;  1-BETA-D-ARABINOFURANOSYLCYTOSINE ;  5-FLUORO-2'-DEOXYURIDINE ;  EFFICIENT ;  OLIGONUCLEOTIDES ;  HYDROLYSIS
语种: 英语
原文出处: 查看原文
WOS记录号: WOS:000263218500014
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/102267
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.S China Univ Technol, Coll Light Ind & Food Sci, Lab Appl Biocatalysis, Guangzhou 510640, Peoples R China
2.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

Recommended Citation:
Li, Ning,Zong, Min-Hua,Ma, Ding. Regioselective acylation of nucleosides and their analogs catalyzed by Pseudomonas cepacia lipase: enzyme substrate recognition[J]. TETRAHEDRON,2009,65(5):1063-1068.
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