Cluster glycosides and heteroglycoclusters presented in alternative arrangements

Figueredo, Andreza S., Zamoner, Luis O. B., Rejzek, Martin, Field, Robert A. ORCID: https://orcid.org/0000-0001-8574-0275 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:	04 Nov 2024 14:30
URI:	https://ueaeprints.uea.ac.uk/id/eprint/96498
DOI:	10.1016/j.tetlet.2018.10.069

Actions (login required)

View Item