Synthesis of Tn and Sialyl Tn Building Blocks for Solid Phase Glycopeptide Synthesis

Article abstract of DOI:10.1016/0040-4039(95)01515-9

Tn (GalNAcα1 -> O-Thr) and sialyl Tn (NeuAcα2 -> 6GalNAcα1 -> O-Thr) building blocks for direct use in Fmoc solid phase glycopeptide synthesis have been prepared in 3 and 5 steps, respectively, from p-cresyl 2-azido-2-deoxy-3,6-di-O-tert-butyldimethylsilyl-1-thio-β-D-galactopyranoside (3).The silyl protective groups used for the GalNAc moiety of the Tn building block may be removed simultaneously with glycopeptide cleavage from the solid phase under acidic conditions.