Abstract
The globotriaosylceramide (Gb3) verotoxin (VT) interaction is one of several examples of glycolipid receptors where the ceramide (or lipid) free oligosaccharides fail to show the expected binding parameters. We present a novel, yet simple strategy to synthesize monovalent, water soluble glycosphingolipid mimics which retain receptor function. Replacing the fatty acid chain with rigid, three dimensional hydrocarbon frames, such as adamantane, gives a novel class of neohydrocarbon glycoconjugates. Such adamantyl conjugates derived from Gb3showed significantly enhanced solubility in water compared to natural Gb3. Adamantyl-Gb3showed a thousand fold enhanced inhibitory activity (IC50= 1 μM) for VT-Gb3binding as compared to a lipid free Gb3oligosaccharide derivative, αGal1-4βGal1-4βGlc1-O-CH2CH(CH2SO2C4H9)2(IC50> 2 mM). This represents a new approach to the generation of antagonists of glycolipid receptors.
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