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Regioselective Acylation of Nucleosides Catalyzed by Candida Antarctica Lipase B: Enzyme Substrate Recognition
Li, Ning1,2; Zong, Min-Hua1; Ma, Ding2; Ma D(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
2008-11-01
DOI10.1002/ejoc.200800780
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
关键词[WOS]SOLUTION-PHASE SYNTHESIS ; ACID ESTER PRODRUGS ; BUILDING-BLOCKS ; IONIC LIQUID ; 1-BETA-D-ARABINOFURANOSYLCYTOSINE ; FLOXURIDINE ; EFFICIENT ; OLIGONUCLEOTIDES ; CHEMOTHERAPY ; BIOCATALYST
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)
语种英语
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WOS记录号WOS:000261756900002
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被引频次:22[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://cas-ir.dicp.ac.cn/handle/321008/101039
专题中国科学院大连化学物理研究所
通讯作者Ma D(马丁); M. Zong
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
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Li, Ning,Zong, Min-Hua,Ma, Ding,et al. Regioselective Acylation of Nucleosides Catalyzed by Candida Antarctica Lipase B: Enzyme Substrate Recognition[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2008(32):5375-5378.
APA Li, Ning,Zong, Min-Hua,Ma, Ding,马丁,&M. Zong.(2008).Regioselective Acylation of Nucleosides Catalyzed by Candida Antarctica Lipase B: Enzyme Substrate Recognition.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(32),5375-5378.
MLA Li, Ning,et al."Regioselective Acylation of Nucleosides Catalyzed by Candida Antarctica Lipase B: Enzyme Substrate Recognition".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .32(2008):5375-5378.
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