Generation of α-Linked Oligosaccharide Libraries by Random Glycosylation on Unprotected Acceptors

Abstract

Background: The GlcNAc related disaccharides were reported to show inhibitory activity on breast tumor cells (MDAMB- 231). However, synthesis of disaccharides is lengthy, laborious and time consuming, and it is necessary to find more efficient methods to generate the disaccharide libraries. Random glycosylation has been an established practice to generate β-linked disaccharides library. Synthesis of α-linked disaccharide libraries by random glycosylation hasn’t been explored yet. We present our results on the synthesis of α-linked GlcNAc related disaccharide libraries by random glycosylation in this article. Results: Employing random glycosylation as a key step on an unprotected GlcNAc monosaccharide, and after deprotection and careful purification, few α-linked GlcNAc related disaccharide libraries were obtained in acceptable ratios, and the results were confirmed by mass and NMR spectral data. Conclusion: Random glycosylation was demonstrated as an efficient method for the synthesis of α-linked GlcNAc related oligosaccharide libraries.