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Synthesis and affinity evaluation of a small library of bidentate cholera toxin ligands: towards nonhydrolyzable ganglioside mimics
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2010 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, no 6, p. 1951-1967Article in journal (Refereed) Published
Abstract [en]

A small library of nonhydrolyzable mimics of GM1 ganglioside, featuring galactose and sialic acid its pharmacophoric carbohydrate residues,, was synthesized and tested. All compounds were synthesized from readily available precursors using high-performance reactions, including click chemistry protocols, and avoiding O-glycosidic bonds. Sonic of the most active molecules also feature a point of further derivatization that can be used for conjugation will, polyvalent aglycons. Their affinity towards cholera toxin was assessed by weak affinity chromatography, which allowed a systematic evaluation and selection of the best candidates. Affinity could be enhanced up to one or two orders of magnitude over the affinity of the individual pharmacophoric sugar residues.

Place, publisher, year, edition, pages
2010. Vol. 16, no 6, p. 1951-1967
National Category
Organic Chemistry
Research subject
Natural Science, Biotechnology; Natural Science; Natural Science, Biochemistry; Natural Science, Organic Chemistry
Identifiers
URN: urn:nbn:se:lnu:diva-2034DOI: 10.1002/chem.200902469OAI: oai:DiVA.org:lnu-2034DiVA, id: diva2:309082
Available from: 2010-04-06 Created: 2010-04-06 Last updated: 2017-12-12Bibliographically approved

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Bergström, Maria

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