ANTIGENES DE GROUPE SANGUIN. SYNTHESE DE GLYCOPEPTIDES TN REPRESENTANT LA PARTIE N-TERMINALE DE LA GLYCOPHORINE HUMAINE AN ET AMc

Article abstract of DOI:10.1016/S0040-4020(01)96557-3

This report describes the first synthesis of the triglycosylated pentapeptides H2N-Leu-Ser*-Thr*-Thr*-Glu-OH and H2N-Ser-Ser*-Thr*-Thr*-Glu-OH, in which * represents the 2-acetamido-2-deoxy-α-D-galactopyranosyl residues.These compounds constitute the antigenic aminoterminal portions of respectively human glycophorin A^N and A^Mc.The above compounds were obtained by a stepwise peptide coupling strategy in solution, begining at the C terminus and proceeding toward the N-terminus, using amino acids or suitably protected and activated O-glycosyl-amino acids.Carbohydrate residues were introduced into the sequence as 2-azido-2-deoxy-α-D-galactopyranosyl-L-serine and L-threonine derivatives obtained from the reducing sugar and amino acid by the trifluoromethanesulfonic anhydride procedure.Reduction of the azido functions followed by acetylation and catalytic hydrogenolysis afforded the above antigenic T_N glycosylated pentapeptides.