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题名: Regioselective Acylation of Nucleosides Catalyzed by Candida Antarctica Lipase B: Enzyme Substrate Recognition
作者: Li, Ning1, 2;  Zong, Min-Hua1;  Ma, Ding2
通讯作者: 马丁 ;  M. Zong
关键词: Regioselective acylation ;  Candida antarctica lipase B ;  Substrate recognition ;  Enzyme catalysis ;  Nucleosides
刊名: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
发表日期: 2008-11-01
DOI: 10.1002/ejoc.200800780
期: 32, 页:5375-5378
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 Candida antarctica lipase B (CAL-B) in the acylation of nucleosides was revealed through rational substrate engineering for the first time. CAL-B displayed lower activities and excellent 5'-regioselectivities (94 to >99 %) in the acylation of ribonucleosides 1f-1j as compared to those in the acylation of 2'-deoxynucleosides tale. The excellent regioselectivities might be attributed to the favorable steric hindrance of the 2'-hydroxy group present in ribonucleosides 1f-1j, which destabilizes the conformation of the 3'-acylation transition state in the acylation of 1f-1j and thus reduces the amount of the minor regioisomer. The study of the acyl chain-length specificity showed that CAL-B was more specific toward short-chain fatty acid vinyl esters, especially vinyl butyrate. ( (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
关键词[WOS]: SOLUTION-PHASE SYNTHESIS ;  ACID ESTER PRODRUGS ;  BUILDING-BLOCKS ;  IONIC LIQUID ;  1-BETA-D-ARABINOFURANOSYLCYTOSINE ;  FLOXURIDINE ;  EFFICIENT ;  OLIGONUCLEOTIDES ;  CHEMOTHERAPY ;  BIOCATALYST
语种: 英语
原文出处: 查看原文
WOS记录号: WOS:000261756900002
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/101039
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 Catalyzed by Candida Antarctica Lipase B: Enzyme Substrate Recognition[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2008(32):5375-5378.
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