A highly alpha-selective glycosylation for the convenient synthesis of repeating alpha-(1-->4)-linked N-acetyl-galactosamine units.
The repeating GalpNAc-alpha-(1-->4)-GalpNAc unit is part of a series of essential structures that can be found in many important biomolecules such as the glycoproteins and the O-antigenic polysaccharides of clinically important bacterial strains. In this paper, we describe an exclusive alpha-selective glycosylation reaction, using a 4,6-di-O-tert-butyldimethylsilyl-N-acetyloxazolidinone-protected thioglycoside as the glycosyl donor, under pre-activation conditions, with only half amount of the promoter, providing the product GalpNAc-alpha-(1-->4)-GalpNAc in high isolated yield. This reaction can be also applied to increasing the length of the repeating structure, which is of significant use in further synthesis of branched or linear oligosaccharides.
Yang
Lin
L
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Xue Yuan Road 38, Beijing 100191, China.
Ye
Xin-Shan
XS
D002240:Carbohydrate Sequence; D005688:Galactosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D008969:Molecular Sequence Data; D015394:Molecular Structure; D013237:Stereoisomerism
D005688:Galactosamine