The paper describes the pseudosugar 2 [Gal beta 1-3GalNAc beta 1-4(NeuAc alpha 2-3)DCCHD], a high affinity binder of cholera toxin (CT). The molecule was designed using molecular modeling techniques to mimic the natural CT membrane receptor, ganglioside GM1. The central residue of GM1, a 3,4-disubstituted galactose unit, was recognized as the ganglioside scaffold element and substituted with a conformationally locked cyclohexanediol (DCCHD). DCCHD was synthesized in enantiopure form using enantioselective Diels Alder methodology and regioselectively alpha-sialylation at the equatorial position. Glycosylation with a Gal beta(1-3)GalNAc donor completed the synthesis of 2. The solution structure of 2 and its binding ability to CT were found to be analogous to those of the GM1 oligosaccharide.
Sugar mimics: An artificial receptor for cholera toxin / A. Bernardi, A. Checchia, P. Brocca, S. Sonnino, F. Zuccotto. - In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. - ISSN 0002-7863. - 121:10(1999), pp. 2032-2036.
Sugar mimics: An artificial receptor for cholera toxin
A. BernardiPrimo
;P. Brocca;S. SonninoPenultimo
;
1999
Abstract
The paper describes the pseudosugar 2 [Gal beta 1-3GalNAc beta 1-4(NeuAc alpha 2-3)DCCHD], a high affinity binder of cholera toxin (CT). The molecule was designed using molecular modeling techniques to mimic the natural CT membrane receptor, ganglioside GM1. The central residue of GM1, a 3,4-disubstituted galactose unit, was recognized as the ganglioside scaffold element and substituted with a conformationally locked cyclohexanediol (DCCHD). DCCHD was synthesized in enantiopure form using enantioselective Diels Alder methodology and regioselectively alpha-sialylation at the equatorial position. Glycosylation with a Gal beta(1-3)GalNAc donor completed the synthesis of 2. The solution structure of 2 and its binding ability to CT were found to be analogous to those of the GM1 oligosaccharide.Pubblicazioni consigliate
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