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

A key disaccharide unit in heparin, O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha- D-glucopyranosyl)-(1-->4)-2-O-sulfo-alpha-L-idopyranosyluronic acid, was pr eviously found to be responsible for the binding interaction of heparin to platelets. A clustering effect to enhance the binding was found to be depen dent on the number and frequency of the disaccharide units in a heparin mol ecule. To systematically examine the clustering effect, three oligomer-mode l compounds containing two or three units of the disaccharide were synthesi zed. These compounds inhibited H-3-Iabelled heparin binding to human platel ets more strongly than a compound containing only one unit of the disacchar ide, (C) 1999 Elsevier Science Ltd. All rights reserved.