Intramolecular carbohydrate-aromatic interactions and intermolecular van der Waals interactions enhance the molecular recognition ability of GMI glycomimetics for cholera toxin
Articolo
Data di Pubblicazione:
2004
Citazione:
Intramolecular carbohydrate-aromatic interactions and intermolecular van der Waals interactions enhance the molecular recognition ability of GMI glycomimetics for cholera toxin / A. Bernardi, D. Arosio, D. Potenza, I. Sanchez-Medina, S. Mari, F. Javier Cañada, J. Jimenez-Barbero. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 10:18(2004), pp. 4395-4406.
Abstract:
The design and synthesis of two GM1 glycomimetics, 6 and 7, and nalysis of their conformation in the free state free state and when complexed to cholera toxin is described. These compounds,compounds,
which include an (R)-cyclohexyllactic
acid and an (R)-phenyllactic
acid fragment, respectively, display significant affinity for cholera toxin. A detailed NMR spectroscopy study of the
toxin/glycomimetic complexes, assisted by molecular modeling techniques, has allowed their interactions with the
toxin to be explained at the atomic
level. It is shown that intramolecular
van der Waals and CH–p carbohydrate–aromatic interactions define the conformational properties of 7, which adopts a three-dimensional structure significantly preorganized for proper interaction with the toxin. The exploitation of this kind of sugar–aromatic interaction, which is very well described in the context of carbohydrate/protein
complexes, may open new avenues
for the rational design of sugar mimics.
conformational properties of 7, which
adopts a three-dimensional structure
significantly preorganized for proper
interaction with the toxin. The exploitation
of this kind of sugar–aromatic
interaction, which is very well described
in the context of carbohydrate/protein
complexes, may open new avenues
for the rational design of sugar mimics.
which include an (R)-cyclohexyllactic
acid and an (R)-phenyllactic
acid fragment, respectively, display significant
affinity for cholera toxin. A detailed
NMR spectroscopy study of the
toxin/glycomimetic complexes, assisted by molecular modeling techniques, has
allowed their interactions with the
toxin to be explained at the atomic
level. It is shown that intramolecular
van der Waals and CH–p carbohydrate
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Carbohydrate-aromatic interactions; Carbohydrate-protein interactions; Cholera toxin; Glycomimetics; Oligosaccharides
Elenco autori:
A. Bernardi, D. Arosio, D. Potenza, I. Sanchez-Medina, S. Mari, F. Javier Cañada, J. Jimenez-Barbero
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