Beilstein J. Org. Chem.2014,10, 2539–2549, doi:10.3762/bjoc.10.265
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-acylatedhomoserinelactones (AHLs). The series of novel analogues consists of α-chloro, α-bromo and α-iodo AHL analogues
. 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.
Keywords: halogenated fatty acids; halogenation; N-acylatedhomoserinelactones
reports supporting this theory, it has to be noted that this view point has been challenged and is still under debate among scientists [6][7]. Most Gram-negative bacteria use N-acylatedhomoserinelactones (AHLs) as signal molecules [8]. The general structure of these compounds consist of a lactone ring
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Graphical Abstract
Figure 1:
Structure of N-acyl homoserine lactone (AHL) and putative n→π* interaction. Attenuation of n→π* int...