Journal
CARBOHYDRATE RESEARCH
Volume 345, Issue 12, Pages 1713-1721Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2010.05.031
Keywords
Glycosylation; alpha-Stereoselectivity; alpha-(1 -> 4)-Linked N-acetyl-galactosamine; Oxazolidinone; Thioglycoside
Funding
- National Natural Science Foundation of China [20732001]
- Ministry of Science and Technology of China [2009ZX09501-011]
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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. (C) 2010 Elsevier Ltd. All rights reserved.
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