Synthesis of clustered D-GalNAc (Tn) and D-Galβ(1→3)GalNAc (T) antigenic motifs using a pentaerythritol scaffold

Abstract

The tris(aminoethyl) and triamino derivatives of pentaerythritol have been used as scaffolds or templates for the attachment of immunologically relevant carbohydrates such as D-Galβ(1→3)GalNAc (T) and GalNAc (Tn), through amide linkages with the respective α-glycolyl and α-N-acetyl-L-serinyl glycosides. These clustered glycosidic motifs are intended as haptens for use in the preparation of tumor specific carbohydrate antigens and vaccines. Key words: glycoside synthesis, 2-thiopyridyl carbonate, glycosyl donors and glycopeptide motifs