Synthesis of a trisaccharide of 3-deoxy-D-manno-2-octulopyranosylonic acid (KDO) residues related to the genus-specific lipopolysaccharide epitope of Chlamydia.
The disaccharides, O-(sodium 3-deoxy-alpha- and -beta-D-manno-2-octulopyranosylonate)-(2----8)-sodium (allyl 3-deoxy-alpha-D-manno-2-octulopyranosid)onate, were prepared via glycosylation of methyl (allyl 4,5,7-tri-O-acetyl-3-deoxy-alpha-D-manno-2-octulopyranosid)onat e with methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-D-manno-2-octulopyranosyl bromide)onate under Helferich and Koenigs-Knorr conditions, respectively. Based on g.l.c.-m.s. data of the alpha- and beta-(2----8)-linked disaccharide derivatives, obtained after carbonyl- and carboxyl-group reduction, followed by methylation, the alpha-anomeric configuration was assigned to the terminal KDO-residue in the KDO-region of Chlamydial lipopolysaccharide. The trisaccharide O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2----8)-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2----4)-sodium (allyl 3-deoxy-alpha-D-manno-2-octulopyranosid)onate was obtained via block synthesis using an alpha-(2----8)-linked disaccharide bromide derivative as the glycosyl donor. Copolymerization of the allyl glycosides with acrylamide gave water-soluble macromolecular antigens, suitable for defining epitope specificities of monoclonal antibodies directed against Chlamydial LPS.
Kosma
P
P
Institut für Chemie, Universität für Bodenkultur Wien, Vienna, Austria.
Schulz
G
G
Brade
H
H
D020106:Acrylamide; D000178:Acrylamides; D000942:Antigens, Bacterial; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D055598:Chemical Phenomena; D002621:Chemistry; D002689:Chlamydia / Q000276:immunology*; D002849:Chromatography, Gas; D004187:Disaccharides / Q000138:chemical synthesis; D008401:Gas Chromatography-Mass Spectrometry; D006031:Glycosylation; D008070:Lipopolysaccharides; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008969:Molecular Sequence Data; D015394:Molecular Structure; D011108:Polymers; D013400:Sugar Acids; D014312:Trisaccharides / Q000138:chemical synthesis*
D000178:Acrylamides; D000942:Antigens, Bacterial; D004187:Disaccharides; D008070:Lipopolysaccharides; D011108:Polymers; D013400:Sugar Acids; D014312:Trisaccharides; C002532:2-keto-3-deoxyoctonate; D020106:Acrylamide