Facile and regioselective enzymatic 5鈥?galactosylation of pyrimidine 2鈥?deoxynucleosides catalyzed by 尾-glycosidase from bovine liver

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• 作者：Min Ye^a ; Li-Qiang Yan^a ; Ning Li^b ; ^{lining@scut.edu.cn} ; Min-Hua Zong^b ; ^{btmhzong@scut.edu.cn}
• 关键词：Active glycosy donor ; Enzymatic glycosylation ; Enzyme substrate recognition ; 尾-Galactosidase ; Nucleosides
• 刊名：Journal of Molecular Catalysis B ; Enzymatic
• 出版年：2012
• 期刊代码：55_13811177
• 类别：ce
• 出版时间：July, 2012
• 卷：79
• 期：Complete
• 页码：35-40
• 文件大小：510 K

摘要

A regioselective enzymatic approach to 5鈥?O-galactosylated derivatives of pyrimidine 2鈥?deoxynucleosides was described. With o-nitrophenyl 尾-d-galactoside as glycosyl donor, galactosylation reactions of 2鈥?deoxynucleosides were mediated by a commercial 尾-galactosidase from bovine liver, affording 5鈥?O-galactosylated derivatives with the yields of 45-85%and 5鈥?regioselectivities of 92-100%. The study of enzyme substrate recognition revealed that the 尾-galactosidase performance showed a clear dependence on R-group present in the base moiety of 2鈥?deoxynucleoside. Besides, such desirable products were synthesized with satisfactory yields (41-68%) and moderate to high 5鈥?regioselectivities (87-100%) by using the crude enzyme extract.