Cluster glycosides and heteroglycoclusters presented in alternative arrangements
| Autor: | Martin Rejzek, Andreza S. Figueredo, Ivone Carvalho, Luis Otávio B. Zamoner, Robert A. Field |
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| Rok vydání: | 2018 |
| Předmět: |
Tris
chemistry.chemical_classification biology 010405 organic chemistry Organic Chemistry Iminosugar Glycoside 010402 general chemistry biology.organism_classification 01 natural sciences Biochemistry Combinatorial chemistry Cycloaddition 0104 chemical sciences chemistry.chemical_compound chemistry Drug Discovery Click chemistry Cluster (physics) Tetra Hydroxymethyl |
| Zdroj: | Tetrahedron Letters. 59:4405-4409 |
| ISSN: | 0040-4039 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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