Chemical synthesis of the human Pk-antigenic determinant.
Condensation of 1,2,3, 6-tetra-O-benzoyl-4-O-(2,3,6-tri-O-benzoyl-beta-D-galactopyranosyl) -alpha-D-glucopyranose with 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl chloride in 1,2-dichloroethane in the presence of 2,4,6-trimethylpyridine, silver triflate, and molecular sieve 4 A gave 1,2,3, 6-tetra-O-benzoyl-4-O-[2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-a lpha -D-galactopyranosyl)-beta-D-galactopyranosyl]-alpha-D-glucopyranose. Catalytic hydrogenolysis and debenzoylation then gave 4-O-(4-O-beta-D-galactopyranosyl-beta-D-galactopyranosyl)-D-glucopyranos e, the human blood-group Pk-antigenic determinant. A similar sequence of reaction was performed starting from 1,2,3, 6-tetra-O-benzoyl-4-O-(2,3,6-tri-O-benzoyl-beta-D-galactopyranosyl)-beta -D-glucopyranose.
Jacquinet
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JC
Sinaÿ
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D001789:Blood Group Antigens / Q000276:immunology*; D002236:Carbohydrate Conformation; D000939:Epitopes; D006801:Humans; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009904:Optical Rotation; D010127:P Blood-Group System / Q000276:immunology*; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000276:immunology
D001789:Blood Group Antigens; D000939:Epitopes; D007202:Indicators and Reagents; D010127:P Blood-Group System; D014312:Trisaccharides; C047819:4-O-(4-O-alpha-galactopyranosyl-beta-galactopyranosyl)glucopyranose