Issue 5, 2003
From the journal:

Organic & Biomolecular Chemistry

Mimics of ganglioside GM1 as cholera toxinligands: replacement of the GalNAc residue†

Anna Bernardi,*a   Daniela Arosio,a   Leonardo Manzoni,b   Diego Monti,b   Helena Posteri,a   Donatella Potenza,a   Silvia Maria  and  Jesús Jiménez-Barberoc  

* Corresponding authors

a Universita' di Milano – Dipartimento di Chimica Organica e Industriale e Centro di Eccellenza CISI, via Venezian 21, 20133 Milano, Italy

b CNR-Istituto di Scienze e Tecnologie Molecolari (ISTM), Via Golgi 19, 20133 Milano, Italy

c Dept. de Estructura y Función de Proteínas, Centro de Investigaciones Biológicas CSIC, Velázquez 144, 28006 Madrid, Spain

Abstract

Two new cholera toxin (CT) ligands (4 and 5) are described. The new ligands were designed starting from the known GM1 mimics 2 and 3 by replacement of their GalNAc residue with the C4 isomer GlcNAc. As predicted by molecular modelling, the conformational properties of the equivalent pairs 2–4 and 3–5 are very similar and their affinity for CT is of the same order of magnitude. NMR experiments have also proved that 5 occupies the GM1-binding site of the toxin and have revealed its bound conformation.

Graphical abstract: Mimics of ganglioside GM1 as cholera toxin ligands: replacement of the GalNAc residue

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Article information

DOI
https://doi.org/10.1039/B210503A
Article type
Paper
Submitted
28 Oct 2002
Accepted
13 Dec 2002
First published
05 Feb 2003

Org. Biomol. Chem., 2003,1, 785-792

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Mimics of ganglioside GM1 as cholera toxin ligands: replacement of the GalNAc residue

A. Bernardi, D. Arosio, L. Manzoni, D. Monti, H. Posteri, D. Potenza, S. Mari and J. Jiménez-Barbero, Org. Biomol. Chem., 2003, 1, 785 DOI: 10.1039/B210503A

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