Cluster glycosides and heteroglycoclusters presented in alternative arrangements

Andreza S. Figueredo, Luis O.B. Zamoner, Martin Rejzek, Robert A. Field, Ivone Carvalho

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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.
Original languageUndefined
JournalTetrahedron Letters
Early online date31 Oct 2018
Publication statusPublished - Dec 2018

Research Beacons, Institutes and Platforms

  • Manchester Institute of Biotechnology

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