Synthesis and biological activity of oligomer-model compounds containing units of a key platelet-binding disaccharide of heparin

Abstract A key disaccharide unit in heparin, O -(2-deoxy-2-sulfamido-6- O -sulfo-α- d -glucopyranosyl)-(1→4)-2- O -sulfo-α- l -idopyranosyluronic acid, was previously found to be responsible for the binding interaction of heparin to platelets. A clustering effect to enhance the binding was found to be dependent on the number and frequency of the disaccharide units in a heparin molecule. To systematically examine the clustering effect, three oligomer-model compounds containing two or three units of the disaccharide were synthesized. These compounds inhibited 3 H-labelled heparin binding to human platelets more strongly than a compound containing only one unit of the disaccharide.