Synthesis and biological activity of a model disaccharide containing a key unit in heparin for binding to platelets

Article abstract of DOI:10.1016/0040-4039(95)02346-1

To determine the specific site(s) in heparin necessary for binding to platelets, synthesis of a model compound containing the disaccharide sequence, O-(2-deoxy-2-sulfamido-6-O-sulfo-α-D-glucopyranosyl)-(1→4)-2-O-sulfo- α-L-idopyranuronic acid, found in heparin was performed by α-selective glycosidation using a phenyl thioglycoside as a donor. The compound inhibited ¹²⁵I-labelled heparin binding to human platelets to a greater extent than a heparin-derived disaccharide, obtained by the heparinase I digestion, yet contained the same number of sulfate groups per molecule.