Synthesis of sulfonic acid analogues of the non-reducing end trisaccharide of the antithrombin binding domain of heparin

• DOI: 10.1016/j.tetlet.2010.10.042
• Publication Date: 2010-10-22T10:29:48Z
• Authors: László Lázár; Mihály Herczeg; Anikó Fekete; Anikó Borbás; András Lipták; Sándor Antus
• Keywords: Természettudományok; Kémiai tudományok; 01 natural sciences; 3. Good health; 0104 chemical sciences

Three sulfonic acid trisaccharides related to the antithrombin-binding DEFGH domain of heparin were synthesised. Trisaccharides carrying the sulfonatomethyl moiety at position 2 or 6 were prepared in high yields by [DE+F] couplings using the same disaccharide uronate donor and the appropriate sulfonic acid acceptor, respectively. The trisaccharide with a 3-deoxy-3-sulfonatomethyl function could be obtained with high efficacy by a [D+EF] coupling where the carboxylic function of the EF uronate acceptor was created at a disaccharide level.