Extended targeting potential and improved synthesis of Microcin C analogs as antibacterials
2011
Vondenhoff, Gaston H.M. | Dubiley, Svetlana | Severinov, Konstantin | Lescrinier, Eveline | Rozenski, Jef | Van Aerschot, Arthur
Microcin C (McC) (1) is a potent antibacterial compound produced by some Escherichia coli strains. McC functions through a Trojan-Horse mechanism: it is actively taken up inside a sensitive cell through the function of the YejABEF-transporter and then processed by cellular aminopeptidases. Processed McC (2) is a non-hydrolysable aspartyl-adenylate analog that inhibits aspartyl-tRNA synthetase (AspRS). A new synthesis is described that allows for the production of a wide variety of McC analogs in acceptable amounts. Using this synthesis a number of diverse compounds was synthesized with altered target specificity. Further characteristics of the YejABEF transporters were determined using these compounds.
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