Regioselective synthesis of α-D-glucopyranosiduronic acid derivatives and biological test against bacterial Staphylococcus aureus and Salmonella agona  

作　　者：CASSIDY Seamas 

机构地区：[1]Food Science and Environmental Health Department,Dublin Institute of Technology, Dublin 1, Ireland

出　　处：《Science China Chemistry》2010年第4期877-883,共7页中国科学（化学英文版）

基　　金：supported by DIT’s Research Scholarship Funding and the Applied Chemistry Key Subject of Anhui Province (Grant No. 200802187C)

摘　　要：α-D-Glucopyranosiduronides were stereoselectively synthesized from D-glucopyranosiduronic acid via the intermediate 1,6-lactone. Fatty acid esters were regioselectively introduced at the 2-O-position of α-D-glucopyranosiduronides using dibutyltin dimethoxide as the stannylating agent. Antibacterial tests show that methyl 2-O-lauroyl-O-D-glucopyranosiduronic acid and azido 2-O-lauroyl-O-D-glucopyranosid-uronic acid are effective inhibitors against Staphylococcus aureus.α-D-Glucopyranosiduronides were stereoselectively synthesized from D-glucopyranosiduronic acid via the intermediate 1,6-lactone. Fatty acid esters were regioselectively introduced at the 2-O-position of α-D-glucopyranosiduronides using dibutyltin dimethoxide as the stannylating agent. Antibacterial tests show that methyl 2-O-lauroyl-O-D-glucopyranosiduronic acid and azido 2-O-lauroyl-O-D-glucopyranosid-uronic acid are effective inhibitors against Staphylococcus aureus.

关 键 词：DIBUTYLTIN dimethoxide STEREOSELECTIVITY regioselectivity ANTIBACTERIAL 

分 类 号：R96[医药卫生—药理学]