title: Towards oligosaccharide libraries: a study of the random galactosylation of unprotected N-acetylglucosamine.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Alberta, Edmonton, Canada.
authors.forename: Y
authors.initials: Y
authors.lastname: Ding
authors.forename: J
authors.initials: J
authors.lastname: Labbe
authors.forename: O
authors.initials: O
authors.lastname: Kanie
authors.forename: O
authors.initials: O
authors.lastname: Hindsgaul
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D004187:Disaccharides / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D005690:Galactose / Q000737:chemistry*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D013056:Spectrophotometry, Ultraviolet; D013696:Temperature
chemical_list: D004187:Disaccharides; D000117:Acetylglucosamine; D005690:Galactose