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Investigating the Toxicity of the Aeruginosin Chlorosulfopeptides by Chemical Synthesis

Scherer, Manuel and Bezold, Dominik and Gademann, Karl. (2016) Investigating the Toxicity of the Aeruginosin Chlorosulfopeptides by Chemical Synthesis. Angewandte Chemie International Edition, 55 (32). pp. 9427-9431.

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Official URL: http://edoc.unibas.ch/53480/

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Abstract

Harmful algal blooms are becoming more prevalent all over the world, and identification and mechanism-of-action studies of the responsible toxins serve to protect ecosystems, livestock, and humans alike. In this study, the chlorosulfopeptide aeruginosin 828A, which rivals the well-known toxin microcystin LR in terms of crustacean toxicity, has been synthesized for the first time. Furthermore, three congeners with different permutations of the chloride and sulfate groups were prepared, thereby enabling toxicity studies without the risk of contamination by other natural toxins. Toxicity assays with the sensitive crustacean Thamnocephalus platyurus demonstrated that the introduction of a sulfate group leads to pronounced toxicity, and NMR spectroscopic evidence suggests that the chloride substituent modulates the conformation, which in turn might influence protease inhibition.
Faculties and Departments:05 Faculty of Science > Departement Chemie
05 Faculty of Science > Departement Chemie > Chemie
05 Faculty of Science > Departement Chemie > Former Organization Units Chemistry > Organische Chemie (Gademann)
UniBasel Contributors:Scherer, Manuel and Gademann, Karl
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Wiley
ISSN:1433-7851
e-ISSN:1521-3773
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:25 Jan 2017 15:42
Deposited On:25 Jan 2017 15:41

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