Issue 26, 2013
From the journal:

Organic & Biomolecular Chemistry

Nanomolar cholera toxininhibitors based on symmetrical pentavalent ganglioside GM1os-sym-corannulenes†

Martin Mattarella,‡a   Jaime Garcia-Hartjes,‡b   Tom Wennekes,b   Han Zuilhof*bc  and  Jay S. Siegel*a  

* Corresponding authors

a Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland
E-mail: jss@oci.uzh.ch
Tel: +41 446354281

b Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB, Wageningen, The Netherlands

c Department of Chemical and Materials Engineering, King Abdulaziz University, Jeddah, Saudi Arabia
E-mail: han.zuilhof@wur.nl
Tel: +31 317482361

Abstract

Eight symmetric and pentavalent corannulene derivatives were functionalized with galactose and the ganglioside GM1-oligosaccharide (GM1os) via copper-catalyzed alkyne-azidecycloaddition (CuAAC) reactions. The compounds were evaluated for their ability to inhibit the binding of the pentavalent cholera toxin to its natural ligand, ganglioside GM1. In this assay, all ganglioside GM1os-sym-corannulenes proved to be highly potent nanomolar inhibitors of cholera toxin.

Graphical abstract: Nanomolar cholera toxin inhibitors based on symmetrical pentavalent ganglioside GM1os-sym-corannulenes

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Article information

DOI
https://doi.org/10.1039/C3OB40438B
Article type
Paper
Submitted
03 Mar 2013
Accepted
11 May 2013
First published
04 Jun 2013
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2013,11, 4333-4339

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Nanomolar cholera toxininhibitors based on symmetrical pentavalent ganglioside GM1os-sym-corannulenes

M. Mattarella, J. Garcia-Hartjes, T. Wennekes, H. Zuilhof and J. S. Siegel, Org. Biomol. Chem., 2013, 11, 4333 DOI: 10.1039/C3OB40438B

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