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.
Full text not available from this repository.
Official URL: https://edoc.unibas.ch/71693/
Downloads: Statistics Overview
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 (MPI) > 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 |
Repository Staff Only: item control page