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Issue 37, 2012
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Mutual influence of backbone proline substitution and lipophilic tail character on the biological activity of simplified analogues of caspofungin

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Abstract

The echinocandins represent the most recent class of antifungal drugs. Previous structure–activity relationship studies on these lipopeptides have relied mainly upon semisynthetic derivatives due to their complex chemical structures. A successful strategy for the rapid enantioselective synthesis of the branched fatty acid chain of caspofungin and analogues was developed to synthesize several simplified analogues of caspofungin. The specific minimum inhibitory activity of each mimic was determined against a panel of Candida strains. This approach gave access to new fully synthetic derived caspofungin mimics with high and selective antifungal activities against Candida strains. In addition, the data suggested an important role of the hydroxy proline residue in the bioactive conformation of the macrocyclic peptide ring structure.

Graphical abstract: Mutual influence of backbone proline substitution and lipophilic tail character on the biological activity of simplified analogues of caspofungin

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Article information


Submitted
17 May 2012
Accepted
18 Jul 2012
First published
24 Jul 2012

Org. Biomol. Chem., 2012,10, 7491-7502
Article type
Paper

Mutual influence of backbone proline substitution and lipophilic tail character on the biological activity of simplified analogues of caspofungin

M. P. C. Mulder, P. Fodran, J. Kemmink, E. J. Breukink, J. A. W. Kruijtzer, A. J. Minnaard and R. M. J. Liskamp, Org. Biomol. Chem., 2012, 10, 7491
DOI: 10.1039/C2OB25951F

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