title: A Modular Synthetic Approach to Isosteric Sulfonic Acid Analogues of the Anticoagulant Pentasaccharide Idraparinux.
abstract: 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 differentC-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 fullyO-sulfated,O-methylated sulfonic acid end-products was also studied.
authors.affiliation: Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary. mezzo.erika@science.unideb.hu.
authors.forename: Erika
authors.initials: E
authors.lastname: Mező
authors.affiliation: Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary. eszenyi.daniel@science.unideb.hu.
authors.forename: Dániel
authors.initials: D
authors.lastname: Eszenyi
authors.affiliation: Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary. esztervargaa@gmail.com.
authors.forename: Eszter
authors.initials: E
authors.lastname: Varga
authors.affiliation: Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary. herczeg.mihaly@science.unideb.hu.
authors.forename: Mihály
authors.initials: M
authors.lastname: Herczeg
authors.affiliation: Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary. borbas.aniko@pharm.unideb.hu.
authors.forename: Anikó
authors.initials: A
authors.lastname: Borbás
mesh_terms: D000925:Anticoagulants / Q000138:chemical synthesis / Q000737:chemistry*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D006031:Glycosylation; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D013451:Sulfonic Acids / Q000737:chemistry*
chemical_list: D000925:Anticoagulants; D009844:Oligosaccharides; D013451:Sulfonic Acids; C479958:idraparinux
keywords: carbohydrates; glycosylation; heparin; sulfonic acid; uronic acid