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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Cluster glycosides and heteroglycoclusters presented in alternative arrangements

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Author(s):
Figueredo, Andreza S. [1] ; Zamoner, Luis O. B. [1] ; Rejzek, Martin [2] ; Field, Robert A. [2] ; Carvalho, Ivone [1]
Total Authors: 5
Affiliation:
[1] Univ Sao Paulo, Sch Pharmaceut Sci Ribeirao Preto, Ave Cafe S-N, BR-14040903 Ribeirao Preto - Brazil
[2] John Innes Ctr, Dept Biol Chem, Norwich Res Pk, Norwich NR4 7UH, Norfolk - England
Total Affiliations: 2
Document type: Journal article
Source: Tetrahedron Letters; v. 59, n. 50, p. 4405-4409, DEC 12 2018.
Web of Science Citations: 1
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. (C) 2018 Elsevier Ltd. All rights reserved. (AU)

FAPESP's process: 13/27038-8 - Synthesis and biological evaluation of glycoclusters with potential antiparasitic, antimicrobial and antitumor activities.
Grantee:Andreza da Silva Figueredo
Support Opportunities: Scholarships in Brazil - Doctorate