Solid phase synthesis of mono- and di-saccharide-containing glycopeptides

Abstract

Derivatives of Fmoc-threonine (Fmoc = fluoren-9-ylmethoxycarbonyl) with O-glycosidically peracetylated β-D-Galp-(1 → 3)-α-D-GalNAcp or α-D-GalNAcp chains have been used in a solid phase synthesis of the oncofetal fibronectin sequence VTHPGY (benzyl protection was used on histidine and tyrosine); a super-acid sensitive resin was used, which enabled the isolation of the protected glycopeptide after synthesis, a feature that substantially facilitated verification of the structure by n.m.r. and m.s.