Syntheses of p-nitrophenyl 3- and 4-thio-β-d-glycopyranosides

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• 作者：Hong-Ming Chen ; Stephen G. Withers
• 关键词：Thiosugars ; Substrate analogs ; Double serial displacement ; Thioglycoligase ; Thioglycosides ; Glycosidase inhibitors
• 刊名：Carbohydrate Research
• 出版年：2010
• 出版时间：10 December 2010
• 年：2010
• 卷：345
• 期：18
• 页码：2596-2604
• 全文大小：476 K

文摘

Thioglycosides have proved to be useful, enzymatically stable analogs of glycosides for structural and mechanistic studies and their synthesis is considerably simplified through the use of thioglycoligases. As part of an investigation into the use of thioglycosides as potential pharmacological chaperones, and as components of glycoproteins and glycolipids, the syntheses of p-nitrophenyl 3-thio-β-d-galactopyranoside, phenyl 1,4-dithio-β-d-glucopyranoside, p-nitrophenyl 4-thio-β-d-mannopyranoside and p-nitrophenyl 2-acetamido-2-deoxy-4-thio-β-d-mannopyranoside are described.