Synthesis of trisaccharides containing 3-deoxy-d-manno-2-octulosonic acid residues related to the KDO-region of enterobacterial lipopolysaccharides

✍ Scribed by Paul Kosma; Gerhard Schulz; Frank M. Unger; Helmut Brade

• Publisher: Elsevier Science
• Year: 1989
• Tongue: English
• Weight: 749 KB
• Volume: 190
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(89)84125-4

✦ Synopsis

Glycosylation of methyl (ally1 7,8-0-carbonyl-3-deoxy-a-D-manno-2-octulopyranosid)onate with an (w-(2+4) linked per-0-acetylated KDO-disaccharide bromide derivative under Helferich conditions afforded a 2: 1 mixture of the (Y-and p-linked trisaccharide derivatives in 50% yield. Removal of the protecting groups gave sodium 0-[sodium (3-deoxy-cr-D-manno-2-octulopyranosyl)onate]-(2~4)-0-[sodium (3-deoxy-aand -P-D-manno-2-octulopyranosyl)onate]-(2-+4)-sodium (ally1 3-deoxy-a-D-manno-2-octulopyranosid)onate.

Radical copolymerization of the ally1 glycosides afforded artificial antigens, suitable for defining antibody specificities directed against the KDO-region of enterobacterial lipapolysaccharides.