Chemical synthesis of the human blood-group P1-antigenic determinant.
Condensation of known benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3,6-tri-O-benzyl-beta-D- galactopyranosyl)-alpha-D-glucopyranoside with 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl chloride in dichloromethane in the presence of 2,4,6-trimethylpyridine, silver triflate, and molecular sieve 4A gave benzyl O-(2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-(1 leads to 4)-O-(2,3,6-tri-O-benzyl-beta-D-galactopyranosyl)-(1 leads to 4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside. Catalytic hydrogenolysis gave crystalline O-alpha-D-galactopyranosyl-(1 leads to 4)-O-beta-D-galactopyranosyl-(1 leads to 4)-2-acetamido-2-deoxy-alpha -D-glucopyranose, the human blood-group P1-antigenic determinant. A similar sequence of reactions was performed starting from allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside, in order to prepare a derivative of this determinant suitable for linkage to carrier molecules.
D001789:Blood Group Antigens / Q000276:immunology*; D000939:Epitopes; D006801:Humans; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010127:P Blood-Group System / Q000276:immunology*; D013329:Structure-Activity Relationship; D014312:Trisaccharides / Q000138:chemical synthesis*
D001789:Blood Group Antigens; D000939:Epitopes; D007202:Indicators and Reagents; C040906:O-alpha-galactopyranosyl(1-4)-O-beta-galactopyranosyl(1-4)-2-acetamido-2-deoxy-alpha-glucopyranose; D009844:Oligosaccharides; D010127:P Blood-Group System; D014312:Trisaccharides