Novel syntheses of Idraparinux, the anticoagulant pentasaccharide with indirect selective factor Xa inhibitory activity

Mihály Herczeg, Erika Mez, László Lázár, Anikó Fekete, K. Kövér, S. Antus, A. Borbás

Research output: Article

15 Citations (Scopus)

Abstract

Idraparinux, the fully O-sulfated, O-methylated, heparin-related pentasaccharide possessing selective factor Xa inhibitory activity, was prepared by two novel synthetic pathways. Each route was based on a 2+3 block synthesis utilizing the same l-iduronic acid-containing trisaccharide acceptor, which was glycosylated with either a glucuronide disaccharide donor or its non-oxidized precursor. The latter route, involving the oxidation of the glucose unit into d-glucuronic acid at a pentasaccharide level proved to be much more efficient, providing the target pentasaccharide in a reasonable overall yield.

Original languageEnglish
Pages (from-to)3149-3158
Number of pages10
JournalTetrahedron
Volume69
Issue number15
DOIs
Publication statusPublished - ápr. 15 2013

Fingerprint

Iduronic Acid
Trisaccharides
Glucuronic Acid
Factor Xa
Disaccharides
Glucuronides
Anticoagulants
Heparin
Glucose
Oxidation
idraparinux
IC 831423

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Novel syntheses of Idraparinux, the anticoagulant pentasaccharide with indirect selective factor Xa inhibitory activity. / Herczeg, Mihály; Mez, Erika; Lázár, László; Fekete, Anikó; Kövér, K.; Antus, S.; Borbás, A.

In: Tetrahedron, Vol. 69, No. 15, 15.04.2013, p. 3149-3158.

Research output: Article

Herczeg, Mihály ; Mez, Erika ; Lázár, László ; Fekete, Anikó ; Kövér, K. ; Antus, S. ; Borbás, A. / Novel syntheses of Idraparinux, the anticoagulant pentasaccharide with indirect selective factor Xa inhibitory activity. In: Tetrahedron. 2013 ; Vol. 69, No. 15. pp. 3149-3158.
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AU - Fekete, Anikó

AU - Kövér, K.

AU - Antus, S.

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