Second generation mimics of ganglioside GM1 as artificial receptors for cholera toxin: replacement of the sialic acid moiety

A Bernardi; L Carrettoni; A G Ciponte; D Monti; S Sonnino

doi:10.1016/s0960-894x(00)00428-5

Second generation mimics of ganglioside GM1 as artificial receptors for cholera toxin: replacement of the sialic acid moiety

Bioorg Med Chem Lett. 2000 Oct 2;10(19):2197-200. doi: 10.1016/s0960-894x(00)00428-5.

Authors

A Bernardi¹, L Carrettoni, A G Ciponte, D Monti, S Sonnino

Affiliation

¹ Dipartimento di Chimica Organica e Industriale, Università di Milano, Italy. anna.bernardi@unimi.it

PMID: 11012028
DOI: 10.1016/s0960-894x(00)00428-5

Abstract

In a program directed towards the design and synthesis of mimics of ganglioside GM1, the NeuAc recognition domain was replaced by simple hydroxy acids, and the affinity of the new ligands to the cholera toxin was determined by fluorescence spectroscopy. The (R)-lactic acid derivative 4 was found to display the highest affinity of the series (KD = 190 microM).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cholera Toxin / metabolism*
G(M1) Ganglioside / analogs & derivatives*
G(M1) Ganglioside / chemical synthesis*
G(M1) Ganglioside / chemistry
G(M1) Ganglioside / metabolism*
Molecular Mimicry*
Molecular Structure
Receptors, Cell Surface / chemistry
Receptors, Cell Surface / metabolism*
Sialic Acids / chemistry
Spectrometry, Fluorescence

Substances

Receptors, Cell Surface
Sialic Acids
choleragen receptor
G(M1) Ganglioside
Cholera Toxin