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Bioorg Med Chem. 1996 May;4(5):683-92.

Towards oligosaccharide libraries: a study of the random galactosylation of unprotected N-acetylglucosamine.

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Department of Chemistry, University of Alberta, Edmonton, Canada.


A single reaction of an unprotected beta-D-GlcNAc glycoside with tetra-O-acetyl-alpha-D-galactopyranosyl trichloroacetimidate in dioxane, catalyzed by BF3-etherate, was shown to yield all six possible Gal-GlcNAc disaccharides. This result is surprising not only because significant amounts of alpha-linked disaccharides were formed, despite the presence of a participating group at O-2 of the glycosyl donor, but also because glycosylation of the primary OH-6 is not the dominant reaction. These results suggest 'random-glycosylation' to be a valid strategy for the rapid production of oligosaccharide libraries.

[Indexed for MEDLINE]

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