title: Toward synthesis of the isosteric sulfonate analogues of the AT-III binding domain of heparin.
abstract: D-glucuronate and l-iduronate containing disaccharides related to the antithrombin-binding pentasaccharide of heparin, in which one of the sulfate esters is systematically replaced by a sodium sulfonatomethyl moiety, were synthesized. The sulfonic acid group was introduced by stereoselective radical addition onto the exomethylene moiety of the appropriate glycoside derivatives, and the resulting sulfonatomethyl glucosides were used as acceptors.
authors.affiliation: Research Group for Carbohydrates of the Hungarian Academy of Sciences, P.O. Box 94, H-4010 Debrecen, Hungary.
authors.forename: Mihály
authors.initials: M
authors.lastname: Herczeg
authors.forename: László
authors.initials: L
authors.lastname: Lázár
authors.forename: Anikó
authors.initials: A
authors.lastname: Borbás
authors.forename: András
authors.initials: A
authors.lastname: Lipták
authors.forename: Sándor
authors.initials: S
authors.lastname: Antus
mesh_terms: D000620:Aminoimidazole Carboxamide / Q000138:chemical synthesis*; D000990:Antithrombin III / Q000737:chemistry*; D001665:Binding Sites; D005965:Glucuronates / Q000138:chemical synthesis / Q000737:chemistry; D006493:Heparin / Q000138:chemical synthesis* / Q000737:chemistry; D007067:Iduronic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009844:Oligosaccharides / Q000737:chemistry*; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry; D013229:Stearic Acids / Q000138:chemical synthesis / Q000737:chemistry; D013329:Structure-Activity Relationship; D013451:Sulfonic Acids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D005965:Glucuronates; D009844:Oligosaccharides; D011719:Pyrazines; D013229:Stearic Acids; D013451:Sulfonic Acids; D007067:Iduronic Acid; D000620:Aminoimidazole Carboxamide; D000990:Antithrombin III; D006493:Heparin; C040995:isostearic acid