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30 october 2014 15:23:01

 
Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators (Beilstein Journal of Organic Chemistry)
 


Abstract Novel N-α-haloacylated homoserine lactones, in which a halogen atom was introduced at the α-position of the carbonyl function of the N-acyl chain, have been studied as quorum sensing (QS) modulators and compared with a library of natural N-acylated homoserine lactones (AHLs). The series of novel analogues consists of α-chloro, α-bromo and α-iodo AHL analogues. Furthermore, the biological QS activity of the synthetic AHL analogues compared to the natural AHLs was evaluated. Halogenated analogues demonstrated a reduced activity in the Escherichia coli JB523 bioassay, with the α-iodo lactones being the less active ones and the α-chloro AHLs the most potent QS agonists. Most of the α-haloacylated analogues did not exhibit a significant reduction when tested in the QS inhibition test. Therefore, these novel analogues could be utilized as chemical probes for QS structure–activity studies. Beilstein J. Org. Chem. 2014, 10, 2539–2549. doi:10.3762/bjoc.10.265


 
361 viewsCategory: Chemistry
 
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