Jump to main content
Jump to site search


Synthesis of multivalent S-glycoside analogs of a heparan sulfate sequence

Author affiliations

Abstract

Glycosaminoglycans (GAGs) are involved in the regulation of a large number of biological processes such as inflammation, cell signalling, angiogenesis, viral infection and coagulation. Unlike molecules isolated from tissues, pure molecules, derived from organic synthesis, can prevent side effects and are very useful tools for understanding the structure–activity relationships of many biological and pharmacological activities. In our research group, we focus particularly on the synthesis of multivalent thioglycoside analogs. In this article, we report on the synthesis of new glycoclusters with thiodisaccharide units, S-analogs of heparan sulfate. The thiodisaccharide analog was obtained by nucleophilic displacement of a 4-triflate galactoside derivative, by an anomeric thiol of a glucuronic acid precursor. After modifying the aglycone part to introduce an azide, the thiodisaccharide was coupled to maltotriose scaffolds carrying one, two or three propargyl groups by CuAAC.

Graphical abstract: Synthesis of multivalent S-glycoside analogs of a heparan sulfate sequence

Back to tab navigation

Supplementary files

Publication details

The article was received on 30 Apr 2019, accepted on 09 Jun 2019 and first published on 11 Jun 2019


Article type: Research Article
DOI: 10.1039/C9QO00581A
Org. Chem. Front., 2019, Advance Article

  •   Request permissions

    Synthesis of multivalent S-glycoside analogs of a heparan sulfate sequence

    D. S. Koffi Teki, A. Bil, V. Moreau, V. Chagnault, B. Fanté, A. Adjou and J. Kovensky, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00581A

Search articles by author

Spotlight

Advertisements