Synthesis and inhibitory activity of a di- and a trisaccharide corresponding to an erythrocyte glycolipid responsible for the nor polyagglutination.

Abstract The polyagglutinable erythrocytes NOR contain unusual neutral glycolipids reactive with anti-NOR antibodies. The disaccharide α- d -Gal p -(1→4)- d -Gal p NAc and the trisaccharide α- d -Gal p -(1→4)-β- d -Gal p NAc-(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)-β- d -GalNAc precursor, and utilized benzyl glycoside and benzyl ether functions for persistent blocking of hydroxyls. The α- d -Gal p -(1→4)-β- d -Gal p NAc 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.