APPLICATION OF THE TRICHLOROACETIMIDATE METHOD TO THE SYNTHESIS OF GLYCOPEPTIDES OF THE MUCIN TYPE CONTAINING A β-D-Galp-(1->3)-D-GalpNAc UNIT

Article abstract of DOI:10.1016/0008-6215(87)80135-0

Mucin-type O-glycopeptides containig the β-D-Galp-(1->3)-D-GalpNAc disaccharide core unit, which is also the T-antigenic determinant, were synthesized from D-galactose, 2-azido-2-deoxy-D-galactose, 2-azido-2-deoxylactose, and L-serine precursors by applying the trichloroacetimidate method.Thus, β-D-Galp-(1->3)-α-D-GalpNAc-(1->3)-Ser (1) and β-D-Galp-(1->4)-β-D-GlcpNAc-(1->6)-<β-D-Galp-(1->3)>-α-D-GalpNAc-(1->3)-Ser (2) were obtained.A protected precursor of 2 having free OH groups at C-4 and C-6 of the inner sugar unit is a valuable intermediate for the synthesis of further O-glycopeptides of this core-unit type.