Development of a Synthetic Receptor for the Food Toxin Beauvericin: A Tale of Carbazole and Steroids

The synthesis of the first synthetic receptor showing high affinity for the toxic ionophoric cyclodepsipeptide beauvericin is described. Binding results in a pronounced increase in fluorescence intensity of the receptor, while this increase is not observed for a very similar ionophore such as valino...

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Bibliographic Details
Published in:Organic letters 2018-10, Vol.20 (20), p.6368-6371
Main Authors: Ornelis, Vincent, Rajkovic, Andreja, Sas, Benedikt, De Saeger, Sarah, Madder, Annemieke
Format: Article
Language:English
Subjects:
Carbazoles - chemistry
Catalysis
Cycloaddition Reaction
Depsipeptides - chemistry
Depsipeptides - metabolism
Ionophores - chemistry
Receptors, Artificial - chemistry
Receptors, Artificial - metabolism
Steroids - chemistry
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Summary:The synthesis of the first synthetic receptor showing high affinity for the toxic ionophoric cyclodepsipeptide beauvericin is described. Binding results in a pronounced increase in fluorescence intensity of the receptor, while this increase is not observed for a very similar ionophore such as valinomycin. Experiments that shed light on the nature of this selectivity are discussed.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02630