Cluster glycosides and heteroglycoclusters presented in alternative arrangements |
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Authors: | Andreza S Figueredo Luis OB Zamoner Martin Rejzek Robert A Field Ivone Carvalho |
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Institution: | 1. School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, Av. do Café s/n, Monte Alegre, Ribeirão Preto 14040-903, Brazil;2. Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich NR4 7UH, UK |
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Abstract: | Multivalent carbohydrates, or glycoclusters, are useful tools to study glycan-lectin and glycan-enzyme recognition processes and have wide potential therapeutic applicability. Herein, we report the synthesis of novel glycoclusters presenting glucopyranose units in alternate arrangements by coupling through the C-1, C-2, C-3 or C-6 sugar positions and using tetra- and hexa-valent scaffolds for multivalent display. Coupling the appropriate azide-functionalised d-glucopyranose units with alkynylated penta- or dipenta-erythritol central cores was accomplished via copper-catalysed azide-alkyne cycloaddition (CuAAC), yielding a panel of eight tetra- and hexa-valent glycoclusters in good yields (52–83%). This click chemistry strategy was extended to the preparation of four heteroglycoclusters using a tris(hydroxymethyl)-aminomethane (TRIS) central scaffold. One unit of either the conventional 1-deoxy-d-nojirymicin iminosugar or its’ C-5 epimeric l-gulo isomer, were incorporated along with three d-glucopyranose units linked through either C-1 or C-6. |
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Keywords: | Multivalency Glycoclusters Heteroglycoclusters Iminosugars CuAAC click reaction |
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