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, A. Lipták, S. Antus, A. Borbás

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

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
JournalTetrahedron
Volume68
Issue number36
DOIs
Publication statusPublished - Sep 9 2012

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Trisaccharides
Sulfonic Acids
Antithrombins
Heparin
Glucuronic Acid
Disaccharides
Acids

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of the non-reducing end trisaccharide of the antithrombin-binding domain of heparin and its bioisosteric sulfonic acid analogues. / Lázár, László; Mez, Erika; Herczeg, Mihály; Lipták, A.; Antus, S.; Borbás, A.

In: Tetrahedron, Vol. 68, No. 36, 09.09.2012, p. 7386-7399.

Research output: Contribution to journalArticle

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AU - Lipták, A.

AU - Antus, S.

AU - Borbás, A.

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