The first synthesis of Neu5Acα2-3Galβ1-4GlcNAcβ1-2Manα1-Ser a newly discovered component of α-dystroglycan

Article abstract of DOI:10.1016/S0040-4039(99)00930-2

Glycopeptide (1), Neu5Acα2-3Galβ1-4GlcNAcβ1-2Manα1-Ser, was synthesized using a chemoenzymatic strategy. Galβ1-4GlcNAcβ1-2Man trisaccharide was prepared using glycosidase assisted oligosaccharide synthesis. After coupling of this trisaccharide with a serine derivative by chemical glycosylation, sialic acid was introduced using sialyltransferase to produce a tetrasaccharide serine derivative. Removal of protecting group afforded glycopeptide (1). Use of a chemoenzymatic strategy allowed for the elimination of numerous synthetic steps and efficient preparation of the target compound.