Ganglioside GM1 mimics: lipophilic substituents improve affinity for cholera toxin

Daniela Arosio; Sergio Baretti; Stefania Cattaldo; Donatella Potenza; Anna Bernardi

doi:10.1016/j.bmcl.2003.07.007

Ganglioside GM1 mimics: lipophilic substituents improve affinity for cholera toxin

Bioorg Med Chem Lett. 2003 Nov 3;13(21):3831-4. doi: 10.1016/j.bmcl.2003.07.007.

Authors

Daniela Arosio¹, Sergio Baretti, Stefania Cattaldo, Donatella Potenza, Anna Bernardi

Affiliation

¹ Dipartimento di Chimica Organica e Industriale, Universita' di Milano, via Venezian 21, 20133 Milan, Italy.

PMID: 14552790
DOI: 10.1016/j.bmcl.2003.07.007

Abstract

Ganglioside GM1 mimics including (R)-2-hydroxy-3-cyclohexylpropionic acid or (R)-2-hydroxy-3-phenylpropionic acid as replacements for NeuAc are stronger cholera toxin binders than the parent ligand 2, which includes (R)-2-hydroxy-propionic acid.

Publication types

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

MeSH terms

Carbohydrate Conformation
Carbohydrate Sequence
Cholera Toxin / chemistry*
G(M1) Ganglioside / chemistry*
Magnetic Resonance Spectroscopy
Molecular Mimicry
Molecular Sequence Data

Substances

G(M1) Ganglioside
Cholera Toxin