Synthesis of trisaccharides containing 3-deoxy-D-manno-2-octulosonic acid residues related to the KDO-region of enterobacterial lipopolysaccharides.
Glycosylation of methyl (allyl 7,8-O-carbonyl-3-deoxy-alpha-D-manno-2-octulo-pyranosid)o nate with an alpha-(2----4) linked per-O-acetylated KDO-disaccharide bromide derivative under Helferich conditions afforded a 2:1 mixture of the alpha- and beta-linked trisaccharide derivatives in 50% yield. Removal of the protecting groups gave sodium O-[sodium (3-deoxy-alpha-D-manno-2-octulopyranosyl)onate]-(2----4)-O-[ sodium (3-deoxy-alpha- and -beta-D-manno-2-octulopyranosyl)onate]-(2----4)-sodium (allyl 3-deoxy-alpha-D-manno-2-octulopyranosid)onate. Radical copolymerization of the allyl glycosides afforded artificial antigens, suitable for defining antibody specificities directed against the KDO-region of enterobacterial lipopolysaccharides.
Kosma
P
P
Institut für Chemie der Universität für Bodenkultur Wien, Vienna, Austria.
Schulz
G
G
Unger
F M
FM
Brade
H
H
D002240:Carbohydrate Sequence; D004755:Enterobacteriaceae; D006031:Glycosylation; D008070:Lipopolysaccharides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis; D013400:Sugar Acids / Q000138:chemical synthesis*; D014312:Trisaccharides / Q000138:chemical synthesis*
D008070:Lipopolysaccharides; D011108:Polymers; D013400:Sugar Acids; D014312:Trisaccharides; C051933:2-octulosonic acid