Regioselective acylation of nucleosides and their analogs catalyzed by Pseudomonas cepacia lipase: enzyme substrate recognition

	Regioselective acylation of nucleosides and their analogs catalyzed by Pseudomonas cepacia lipase: enzyme substrate recognition
	Li, Ning 1,2; Zong, Min-Hua 1; Ma, Ding 2
刊名	tetrahedron
	2009-01-31
卷号	65 期号:5 页码:1063-1068
关键词	Floxuridine Lipase Nucleosides Regioselective acylation Substrate recognition
通讯作者	m. zong ; 马丁
产权排序	2;1
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.
WOS标题词	science & technology ; physical sciences
类目[WOS]	chemistry, organic
研究领域[WOS]	chemistry
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
收录类别	SCI ; IC
原文出处	false
语种	英语
WOS记录号	WOS:000263218500014
公开日期	2010-11-30
内容类型	期刊论文
源URL	[http://159.226.238.44/handle/321008/102267]
专题	大连化学物理研究所_中国科学院大连化学物理研究所
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
推荐引用方式 GB/T 7714	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.
APA	Li, Ning,Zong, Min-Hua,&Ma, Ding.(2009).Regioselective acylation of nucleosides and their analogs catalyzed by Pseudomonas cepacia lipase: enzyme substrate recognition.tetrahedron,65(5),1063-1068.
MLA	Li, Ning,et al."Regioselective acylation of nucleosides and their analogs catalyzed by Pseudomonas cepacia lipase: enzyme substrate recognition".tetrahedron 65.5(2009):1063-1068.