Stereoselective synthesis of lewis-associated trisaccharides as E-selectin inhibitors

Three types of Lewis-associated trisaccharides [the Lea analogs, their epimers with respect to the fucose residue (the 1 c-epi-Lea analogs), and the Lex analogs] were synthesized in a stereoselective manner. Not only the Lea analogs but also the 1 c-epi-Lea analogs inhibited E-selectin-mediated neutrophil accumulation into pleural cavity in lipoteichoic acid-treated mice, with the trend being Lea> 1 c-epi-Lea> Lex.