Synthesis and inhibitory activity of a di- and a trisaccharide corresponding to an erythrocyte glycolipid responsible for the nor polyagglutination.
The polyagglutinable erythrocytes NOR contain unusual neutral glycolipids reactive with anti-NOR antibodies. The disaccharide alpha-D-Galp-(1-->4)-D-GalpNAc and the trisaccharide alpha-D-Galp-(1-->4)-beta-D-GalpNAc-(1-->3)-D-Gal corresponding to the non-reducing end of a NOR glycolipid (NOR1) were chemically synthesized. The syntheses were based on a common (1-->4)-beta-D-GalNAc precursor, and utilized benzyl glycoside and benzyl ether functions for persistent blocking of hydroxyls. The alpha-D-Galp-(1-->4)-beta-D-GalpNAc structural element has been found only recently in Nature, and derivatives thereof have not been synthesized before. Both the synthesized oligosaccharides inhibited specifically human anti-NOR antibodies, the trisaccharide being 300 times more active than the disaccharide.
D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004912:Erythrocytes / Q000737:chemistry* / Q000187:drug effects; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006384:Hemagglutination / Q000187:drug effects*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D004187:Disaccharides; D006017:Glycolipids; D014312:Trisaccharides