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Issue 4, 2017
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Bicyclic enol cyclocarbamates inhibit penicillin-binding proteins

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Natural products form attractive leads for the development of chemical probes and drugs. The antibacterial lipopeptide Brabantamide A contains an unusual enol cyclocarbamate and we used this scaffold as inspiration for the synthesis of a panel of enol cyclocarbamate containing compounds. By equipping the scaffold with different groups, we identified structural features that are essential for antibacterial activity. Some of the derivatives block incorporation of hydroxycoumarin carboxylic acid-amino D-alanine into the newly synthesized peptidoglycan. Activity-based protein-profiling experiments revealed that the enol carbamates inhibit a specific subset of penicillin-binding proteins in B. subtilis and S. pneumoniae.

Graphical abstract: Bicyclic enol cyclocarbamates inhibit penicillin-binding proteins

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The article was received on 02 Aug 2016, accepted on 20 Dec 2016 and first published on 20 Dec 2016

Article type: Paper
DOI: 10.1039/C6OB01664B
Citation: Org. Biomol. Chem., 2017,15, 894-910

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    Bicyclic enol cyclocarbamates inhibit penicillin-binding proteins

    P. Dockerty, J. G. Edens, M. B. Tol, D. Morales Angeles, A. Domenech, Y. Liu, A. K. H. Hirsch, J. Veening, D. Scheffers and M. D. Witte, Org. Biomol. Chem., 2017, 15, 894
    DOI: 10.1039/C6OB01664B

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