Synthesis and biological activity of conformationally constrained sialyl Lewis X analogues with reduced carbohydrate character

Two conformationally constrained analogues of sialyl Lewis X have been synthesised in which the GlcNAc residue has been replaced with cyclohexyl and phenyl rings. The cyclohexyl derived compound was equipotent to sLex and sLea in vitro, suggesting the main role of the GlcNAc residue in sLex is conformational, and represents a simplified inhibitor of adhesion.