Synthesis of new sulfonic acid-containing oligosaccharide mimetics of sialyl Lewis A

Abstract

Two trisaccharides as new sulfonic acid mimetics of the sialyl Lewis A tetrasaccharide were synthesized. The natural sialic acid residue is replaced by a C-sulfonic acid moiety attached to position C-3′ of the lactosamine unit of the mimetics. The l-fucose unit was also replaced by a d-arabinose ring in one of the analogues. Formation of the sulfonic acid moiety on the trisaccharide level could be successfully achieved by means of introduction of an acetylthio moiety into the galactose skeleton and subsequent oxidation. The equatorial arrangement of the acetylthio group linked to C-3 of the galactose ring could be achieved by double nucleophilic substitution; efficient formation of the gulo-triflate derivatives required low-power microwave activation. Oxidation of the acetylthio group was carried out using Oxone in acetic acid.