Synthesis of the non-reducing end trisaccharide of the antithrombin-binding domain of heparin and its bioisosteric sulfonic acid analogues |
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| Authors: | László Lázár Erika Mező Mihály Herczeg András Lipták Sándor Antus Anikó Borbás |
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| Affiliation: | 1. Research Group for Carbohydrates of the Hungarian Academy of Sciences, H-4010 Debrecen, PO Box 94, Hungary;2. Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, PO Box 20, Hungary;3. Department of Pharmaceutical Chemistry, Medical and Health Science Center, University of Debrecen, H-4010 Debrecen, PO Box 70, Hungary |
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| Abstract: | A glucoronic acid-containing trisaccharide related to the antithrombin-binding DEFGH domain of heparin and its methanesulfonic acid analogues were synthesized. Trisaccharides without sulfonic acid content or possessing a sulfonatomethyl moiety at position 2 or 6 of unit F were prepared in high yields by [DE+F] couplings using the same disaccharide uronate donor, respectively. Synthesis of the trisaccharide with a 3-deoxy-3-sulfonatomethyl function was accomplished in three different pathways, from which a [D+EF] coupling and applying a non-oxidized precursor of the glucuronic acid afforded the trisaccharide in the highest yield. |
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