Towards oligosaccharide libraries: a study of the random galactosylation of unprotected N-acetylglucosamine.
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.
Ding
Y
Y
Department of Chemistry, University of Alberta, Edmonton, Canada.
Labbe
J
J
Kanie
O
O
Hindsgaul
O
O
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
D004187:Disaccharides; D000117:Acetylglucosamine; D005690:Galactose