Chemical synthesis of the human blood-group P1-anti-genic determinant

✍ Scribed by Paul-Henri Amvam Zollo; Jean-Claude Jacquinet; Pierre Sinaÿ

• Book ID: 102992231
• Publisher: Elsevier Science
• Year: 1983
• Tongue: English
• Weight: 582 KB
• Volume: 122
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(83)88331-1

✦ Synopsis

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.