Toward synthesis of the isosteric sulfonate analogues of the AT-III binding domain of heparin.
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.
Herczeg
Mihály
M
Research Group for Carbohydrates of the Hungarian Academy of Sciences, P.O. Box 94, H-4010 Debrecen, Hungary.
Lázár
László
L
Borbás
Anikó
A
Lipták
András
A
Antus
Sándor
S
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
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