ABSTRACT: The inhibition of sialyl Lewis X can prevent unwanted cellular extravasation that is associated with inflammatory diseases and tumor metastasis. Described is an efficient methodology to prepare peracetylated GlcNAcβ3Gal-aglycone disaccharides subsequently used as metabolic decoys to inhibit sialyl Lewis X expression. Four glycosides were synthesized from one single parent disaccharide that in turn was prepared by large-scale enzymatic synthesis. The procedure avoids lengthy and inefficient synthetic steps to afford the desired disaccharides quickly with good overall yields.
Journal of Carbohydrate Chemistry. 01/2011; 30(4-6):373-390.