Ganglioside GM1 mimics: Lipophilic substituents improve affinity for cholera toxin

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.

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2003-11, Vol.13 (21), p.3831-3834
Main Authors: AROSIO, Daniela, BARETTI, Sergio, CATTALDO, Stefania, POTENZA, Donatella, BERNARDI, Anna
Format: Article
Language:English
Subjects:
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Bacterial diseases
Biological and medical sciences
Carbohydrate Conformation
Carbohydrate Sequence
Cholera
Cholera Toxin - chemistry
G(M1) Ganglioside - chemistry
Human bacterial diseases
Infectious diseases
Magnetic Resonance Spectroscopy
Medical sciences
Molecular Mimicry
Molecular Sequence Data
Pharmacology. Drug treatments
Tropical bacterial diseases
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Description
Summary: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.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2003.07.007