214767-60-9Relevant articles and documents
Synthesis of a 3-deoxy-L-iduronic acid containing heparin pentasaccharide to probe the conformation of the antithrombin III binding sequence
Lei, Ping-Sheng,Duchaussoy, Philippe,Sizun, Philippe,Mallet, Jean-Maurice,Petitou, Maurice,Sinay, Pierre
, p. 1337 - 1346 (2007/10/03)
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.