Cluster glycosides and heteroglycoclusters presented in alternative arrangements

Figueredo, Andreza S., Zamoner, Luis O. B., Rejzek, Martin, Field, Robert A. and Carvalho, Ivone (2018) Cluster glycosides and heteroglycoclusters presented in alternative arrangements. Tetrahedron Letters, 59 (50). pp. 4405-4409. ISSN 0040-4039

Full text not available from this repository. (Request a copy)

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.

Item Type:	Article
Additional Information:	Funding Information: We acknowledge financial support from Brazilian agencies: FAPESP (Fundação de Amparo à Pesquisa do Estado de São Paulo-Brazil 2013/27038-8) and CNPQ (Conselho Nacional de Desenvolvimento Científico e Tecnológico). Work in the UK was supported by the BBSRC Institute Strategic Program on Understanding and Exploiting Metabolism (MET) [BB/J004561/1] and the John Innes Foundation . Publisher Copyright: © 2018 Elsevier Ltd
Uncontrolled Keywords:	cuaac click reaction,glycoclusters,heteroglycoclusters,iminosugars,multivalency,biochemistry,drug discovery,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1300/1303
Faculty \ School:	Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
Related URLs:	http://www.scopus.com/inward/record.url?...
Depositing User:	LivePure Connector
Date Deposited:	04 Sep 2024 08:33
Last Modified:	06 Feb 2025 12:12
URI:	https://ueaeprints.uea.ac.uk/id/eprint/96498
DOI:	10.1016/j.tetlet.2018.10.069

Actions (login required)

View Item