Bicyclic enol cyclocarbamates inhibit penicillin-binding proteins.
Org Biomol Chem
; 15(4): 894-910, 2017 Jan 25.
Article
em En
| MEDLINE
| ID: mdl-28045164
ABSTRACT
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.
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Base de dados:
MEDLINE
Assunto principal:
Streptococcus pneumoniae
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Bacillus subtilis
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Proteínas de Ligação às Penicilinas
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Antibacterianos
Idioma:
En
Ano de publicação:
2017
Tipo de documento:
Article