Synthesis and NMR spectroscopic investigation of oligosaccharides containing Kdo and L-glycero-D-manno-heptopyranosyl residues.
The disaccharides O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2-->8)-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (8), O-L-glycero-alpha-D-manno-heptopyranosyl-(1-->7)-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (12), and O-alpha-D-mannopyranosyl-(1-->7)-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (21) and the branched trisaccharides O-L-glycero-alpha-D-manno-heptopyranosyl-(1-->7)-[O-(sodium 3-deoxy-alpha- and -beta-D-manno-2-octulopyranosylonate)-(2-->8)]-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (15 and 16) and O-alpha-D-mannopyranosyl-(1-->7)-[O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2-->8)]-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (24) were prepared. Per-O-acetylated mannopyranosyl or Kdo bromide derivatives were employed for the glycosylation steps under Helferich conditions, whereas the imidate derivative 9 was used for the coupling of the L-glycero-D-manno-heptopyranosyl residues. The oligosaccharides were fully characterized by NMR spectroscopic data. Their structures correspond to an artificial linkage pattern providing a potential cross-reactive epitope for antibodies directed against the inner-core-region of enterobacterial as well as chlamydial lipopolysaccharides.
Hofinger
A
A
Institut für Chemie, Universität für Bodenkultur, Vienna, Austria.
Kosma
P
P
Christian
R
R
Bock
K
K
Brade
H
H
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006539:Heptoses; D007202:Indicators and Reagents; D008070:Lipopolysaccharides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry*; D009904:Optical Rotation; D013400:Sugar Acids; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D004187:Disaccharides; D006539:Heptoses; D007202:Indicators and Reagents; D008070:Lipopolysaccharides; D009844:Oligosaccharides; D013400:Sugar Acids; D014312:Trisaccharides; C002532:2-keto-3-deoxyoctonate; C062615:glycero-alpha-manno-heptopyranose