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Synthesis, Biological Evaluation, WAC and NMR Studies of S-Galactosides and Non-Carbohydrate Ligands of Cholera Toxin Based on Polyhydroxyalkylfuroate Moieties
Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
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2013 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 19, no 52, p. 17989-18003Article in journal (Refereed) Published
Abstract [en]

The synthesis of several non-carbohydrate ligands of cholera toxin based on polyhydroxyalkylfuroate moieties is reported. Some of them have been linked to D-galactose through a stable and well-tolerated S-glycosidic bond. They represent a novel type of non-hydrolyzable bidentate ligand featuring galactose and polyhydroxyalkylfuroic esters as pharmacophoric residues, thus mimicking the GM1 ganglioside. The affinity of the new compounds towards cholera toxin was measured by weak affinity chromatography (WAC). The interaction of the best candidates with this toxin was also studied by saturation transfer difference NMR experiments, which allowed identification of the binding epitopes of the ligands interacting with the protein. Interestingly, the highest affinity was shown by non-carbohydrate mimics based on a polyhydroxyalkylfuroic ester structure.

Place, publisher, year, edition, pages
2013. Vol. 19, no 52, p. 17989-18003
Keywords [en]
weak affinity chromatography (WAC), biomimetic synthesis, carbohydrates, cholera toxin, NMR spectroscopy
National Category
Biochemistry and Molecular Biology
Research subject
Natural Science, Biotechnology
Identifiers
URN: urn:nbn:se:lnu:diva-32107DOI: 10.1002/chem.201302786ISI: 000328531000041Scopus ID: 2-s2.0-84891011906OAI: oai:DiVA.org:lnu-32107DiVA, id: diva2:694058
Available from: 2014-02-05 Created: 2014-02-05 Last updated: 2017-12-06Bibliographically approved

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Niss, UlfOhlson, Sten

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CiteExportLink to record
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  • nn-NB
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  • Other locale
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