89025-00-3Relevant articles and documents
ANTIGENES DE GROUPE SANGUIN. SYNTHESE DE GLYCOPEPTIDES TN REPRESENTANT LA PARTIE N-TERMINALE DE LA GLYCOPHORINE HUMAINE AN ET AMc
Ferrari, B.,Pavia, A. A.
, p. 1939 - 1944 (2007/10/02)
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 AN and AMc.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 TN glycosylated pentapeptides.
