Mimics of ganglioside GM1 as cholera toxin ligands: replacement of the GalNAc residue.
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.
Bernardi
Anna
A
Universita' di Milano, Dipartimento di Chimica Organica e Industriale, Centro di Eccellenza CISI, via Venezian 21, 20133 Milano, Italy.
Arosio
Daniela
D
Manzoni
Leonardo
L
Monti
Diego
D
Posteri
Helena
H
Potenza
Donatella
D
Mari
Silvia
S
Jiménez-Barbero
Jesús
J
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
D008024:Ligands; D005677:G(M1) Ganglioside; D002772:Cholera Toxin; D000116:Acetylgalactosamine