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Open AccessArticle

A Modular Synthetic Approach to Isosteric Sulfonic Acid Analogues of the Anticoagulant Pentasaccharide Idraparinux

Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
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Academic Editor: Vito Ferro
Molecules 2016, 21(11), 1497; https://doi.org/10.3390/molecules21111497
Received: 7 September 2016 / Revised: 1 November 2016 / Accepted: 3 November 2016 / Published: 11 November 2016
(This article belongs to the Collection Advances in Glycosciences)
Heparin-based anticoagulants are drugs of choice in the therapy and prophylaxis of thromboembolic diseases. Idraparinux is a synthetic anticoagulant pentasaccharide based on the heparin antithrombin-binding domain. In the frame of our ongoing research aimed at the synthesis of sulfonic acid-containing heparinoid anticoagulants, we elaborated a modular pathway to obtain a series of idraparinux-analogue pentasaccharides bearing one or two primary sulfonic acid moieties. Five protected pentasaccharides with different C-sulfonation patterns were prepared by two subsequent glycosylation reactions, respectively, using two monosaccharide and four disaccharide building blocks. Transformation of the protected derivatives into the fully O-sulfated, O-methylated sulfonic acid end-products was also studied. View Full-Text
Keywords: heparin; carbohydrates; glycosylation; sulfonic acid; uronic acid heparin; carbohydrates; glycosylation; sulfonic acid; uronic acid
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MDPI and ACS Style

Mező, E.; Eszenyi, D.; Varga, E.; Herczeg, M.; Borbás, A. A Modular Synthetic Approach to Isosteric Sulfonic Acid Analogues of the Anticoagulant Pentasaccharide Idraparinux. Molecules 2016, 21, 1497. https://doi.org/10.3390/molecules21111497

AMA Style

Mező E, Eszenyi D, Varga E, Herczeg M, Borbás A. A Modular Synthetic Approach to Isosteric Sulfonic Acid Analogues of the Anticoagulant Pentasaccharide Idraparinux. Molecules. 2016; 21(11):1497. https://doi.org/10.3390/molecules21111497

Chicago/Turabian Style

Mező, Erika; Eszenyi, Dániel; Varga, Eszter; Herczeg, Mihály; Borbás, Anikó. 2016. "A Modular Synthetic Approach to Isosteric Sulfonic Acid Analogues of the Anticoagulant Pentasaccharide Idraparinux" Molecules 21, no. 11: 1497. https://doi.org/10.3390/molecules21111497

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