Beilstein J. Org. Chem.2014,10, 2539–2549, doi:10.3762/bjoc.10.265
Michail Syrpas Ewout Ruysbergh Christian V. Stevens Norbert De Kimpe Sven Mangelinckx Department of Sustainable Organic Chemistry and Technology, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium 10.3762/bjoc.10.265 Abstract Novel N-α-haloacylatedhomoserinelactones, in which a halogen
; N-α-haloacylatedhomoserinelactones; quorum sensing; Introduction
Quorum sensing (QS) is the communication system used by bacteria allowing them to adapt to their environment [1]. Bacteria relying on QS secrete signal molecules, called autoinducers, in order to control the expression of specific
influence of a halogen introduction, the bioactivity of these novel N-α-haloacylatedhomoserinelactones was directly compared with a broad library of naturally occurring AHLs.
Results and Discussion
Synthesis of N-acylated homoserine lactones and halogenated analogues
(S)-Homoserine lactone hydrobromide (1
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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...