Chemoenzymatic synthesis of the branched oligosaccharides which correspond to the core structures of N-linked sugar chains

Abstract

Synthetic routes are described to a partial structure common to all high mannose-type sugar chains and complex-type sugar chains based on a chemoenzymatic strategy which incorporates, (a) enzymatic synthesis of oligosaccharide blocks using glycosidases, and (b) chemical synthesis of the branching oligosaccharides via regioselective coupling. All reaction products correspond to key intermediates necessary for the construction of N-linked oligosaccharides and we have synthesized the branched tetra- manno-oligosaccharide high mannose-type sugar chain and the branched hexa-oligosaccharide complex-type sugar chain using this simple and direct method.