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

László Lázár, Erika Mez, Mihály Herczeg, András Lipták, Sándor Antus, Anikó Borbás

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A glucoronic acid-containing trisaccharide related to the antithrombin-binding DEFGH domain of heparin and its methanesulfonic acid analogues were synthesized. Trisaccharides without sulfonic acid content or possessing a sulfonatomethyl moiety at position 2 or 6 of unit F were prepared in high yields by [DE+F] couplings using the same disaccharide uronate donor, respectively. Synthesis of the trisaccharide with a 3-deoxy-3-sulfonatomethyl function was accomplished in three different pathways, from which a [D+EF] coupling and applying a non-oxidized precursor of the glucuronic acid afforded the trisaccharide in the highest yield.

Original languageEnglish
Pages (from-to)7386-7399
Number of pages14
Issue number36
Publication statusPublished - Sep 9 2012



  • Blood coagulation
  • Glycosylation
  • Heparinoid trisaccharides
  • Sulfonatomethyl analogues
  • d-Glucuronic acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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