Synthesis of a 3-deoxy-L-iduronic acid containing heparin pentasaccharide to probe the conformation of the antithrombin III binding sequence

Article abstract of DOI:10.1016/S0968-0896(98)00127-8

We report in this work the total synthesis of a close analogue of the pentasaccharide active site of heparin, in which the l-iduronic acid residue has been deoxygenated at position three. ¹H NMR studies demonstrated that, as anticipated, such a modification induces a shift of the conformational equilibrium toward ¹C₄ (contribution to the conformational equilibrium rises from 37% to 65%) and a substantial decrease of the affinity for antithrombin III (K(d) 0.154μM versus 0.050μM). Copyright (C) 1998 Elsevier Science Ltd.