title: Mimics of ganglioside GM1 as cholera toxin ligands: replacement of the GalNAc residue.
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.
authors.affiliation: Universita' di Milano, Dipartimento di Chimica Organica e Industriale, Centro di Eccellenza CISI, via Venezian 21, 20133 Milano, Italy.
authors.forename: Anna
authors.initials: A
authors.lastname: Bernardi
authors.forename: Daniela
authors.initials: D
authors.lastname: Arosio
authors.forename: Leonardo
authors.initials: L
authors.lastname: Manzoni
authors.forename: Diego
authors.initials: D
authors.lastname: Monti
authors.forename: Helena
authors.initials: H
authors.lastname: Posteri
authors.forename: Donatella
authors.initials: D
authors.lastname: Potenza
authors.forename: Silvia
authors.initials: S
authors.lastname: Mari
authors.forename: Jesús
authors.initials: J
authors.lastname: Jiménez-Barbero
mesh_terms: D000116:Acetylgalactosamine / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002772:Cholera Toxin / Q000737:chemistry*; D005677:G(M1) Ganglioside / Q000737:chemistry*; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D018716:Molecular Mimicry; D008969:Molecular Sequence Data
chemical_list: D008024:Ligands; D005677:G(M1) Ganglioside; D002772:Cholera Toxin; D000116:Acetylgalactosamine