Problems and Progress in Glycopeptide Synthesis

Abstract

The contribution of the N- and O-linked oligosaccharides to a variety of glycoprotein-mediated biological phenomena has recently attracted broad interest. Synthetic glycopeptides are needed as the tools to ascertain the biological roles played by the oligosaccharides. A series of investigations on glycopeptide synthesis thus far made in our research group is presented in this minireview. In order to facilitate the construction of N- and O-linked oligosaccharides, we have been employing a benzyl group for protection of the hydroxyl groups. Having thus prepared glycosylated amino acid building blocks, we tackled the solid-phase synthesis of glycopeptides. Syntheses of the part structures of such biologically important glycoproteins as glycophorin, leukosialin, α2HS glycoprotein, hCG, CD52, and emmprin are described.