Synthesis, biological evaluation, WAC and NMR studies of S-galactosides and non-carbohydrate ligands of cholera toxin based on polyhydroxyalkylfuroate moieties

Ramos-Soriano, Javier, Niss, Ulf, Angulo, Jesus ORCID: https://orcid.org/0000-0001-7250-5639, Angulo, Manuel, Moreno-Vargas, Antonio J., Carmona, Ana T., Ohlson, Sten and Robina, Inmaculada (2013) Synthesis, biological evaluation, WAC and NMR studies of S-galactosides and non-carbohydrate ligands of cholera toxin based on polyhydroxyalkylfuroate moieties. Chemistry - A European Journal, 19 (52). 17989–18003. ISSN 0947-6539

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Abstract

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.

Item Type:	Article
Uncontrolled Keywords:	weak affinity chromatography (wac),biomimetic synthesis,carbohydrates,cholera toxin,nmr spectroscopy,sdg 3 - good health and well-being ,/dk/atira/pure/sustainabledevelopmentgoals/good_health_and_well_being
Faculty \ School:	Faculty of Science > School of Pharmacy (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Drug Delivery and Pharmaceutical Materials (former - to 2017) Faculty of Science > Research Groups > Pharmaceutical Materials and Soft Matter
Depositing User:	Pure Connector
Date Deposited:	06 Jan 2014 14:42
Last Modified:	25 Sep 2024 11:05
URI:	https://ueaeprints.uea.ac.uk/id/eprint/47095
DOI:	10.1002/chem.201302786

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