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Configurationally stabilized analogs of M. ulcerans exotoxins mycolactones A and B reveal the importance of side chain geometry for mycolactone virulence

Gehringer, Matthias and Mäder, Patrick and Gersbach, Philipp and Pfeiffer, Bernhard and Scherr, Nicole and Dangy, Jean-Pierre and Pluschke, Gerd and Altmann, Karl-Heinz. (2019) Configurationally stabilized analogs of M. ulcerans exotoxins mycolactones A and B reveal the importance of side chain geometry for mycolactone virulence. Organic Letters, 21 (15). pp. 5853-5857.

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Official URL: https://edoc.unibas.ch/71693/

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Abstract

Mycolactones A/B (1a/b) are exotoxins of Mycobacterium ulcerans that are the molecular cause of Buruli ulcer. 1a/b represent a rapidly equilibrating mixture of Z/E isomers about the C4' horizontal lineC5' double bond of the C5-side chain. Here, we describe the syntheses of mycolactone analogs with configurationally stable C5-side chains (2a, E mimetic; 2b/c, Z mimetics). Based on the cytotoxicity of 2a-c, the Delta(4',5')-trans isomer of mycolactones A/B (1b) appears to be the major virulence factor.
Faculties and Departments:09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH)
09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology > Molecular Immunology (Pluschke)
UniBasel Contributors:Scherr, Nicole and Dangy, Jean-Pierre
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
ISSN:1523-7060
e-ISSN:1523-7052
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:19 Aug 2019 13:36
Deposited On:19 Aug 2019 13:36

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