Journal
TETRAHEDRON LETTERS
Volume 59, Issue 50, Pages 4405-4409Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2018.10.069
Keywords
Multivalency; Glycoclusters; Heteroglycoclusters; Iminosugars; CuAAC click reaction
Categories
Funding
- FAPESP (Fundacao de Amparo a Pesquisa do Estado de Sao Paulo-Brazil) [2013/27038-8]
- CNPQ(Conselho Nacional de Desenvolvimento Cientifico e Tecnologico)
- BBSRC Institute Strategic Program on Understanding and Exploiting Metabolism (MET) [BB/J004561/1]
- John Innes Foundation
- BBSRC [BBS/E/J/000C0618, BBS/E/J/000PR9790] Funding Source: UKRI
Ask authors/readers for more resources
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available