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Issue 39, 2014
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Inhibition of quorum sensing and biofilm formation in Vibrio harveyi by 4-fluoro-DPD; a novel potent inhibitor of AI-2 signalling

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Abstract

(S)-4,5-Dihydroxypentane-2,3-dione [(S)-DPD, (1)] is a precursor for AI-2, a quorum sensing signalling molecule for inter- and intra-species bacterial communication. The synthesis of its fluoro-analogue, 4-fluoro-5-hydroxypentane-2,3-dione (2) is reported. An intermediate in this route also enables a new, shorter synthesis of the native (S)-DPD. 4-Fluoro-DPD (2) completely inhibited bioluminescence and bacterial growth of Vibrio harveyi BB170 strain at 12.5 μM and 100 μM, respectively.

Graphical abstract: Inhibition of quorum sensing and biofilm formation in Vibrio harveyi by 4-fluoro-DPD; a novel potent inhibitor of AI-2 signalling

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Supplementary files

Article information


Submitted
20 Dec 2013
Accepted
07 Mar 2014
First published
07 Mar 2014

Chem. Commun., 2014,50, 5000-5002
Article type
Communication
Author version available

Inhibition of quorum sensing and biofilm formation in Vibrio harveyi by 4-fluoro-DPD; a novel potent inhibitor of AI-2 signalling

M. Kadirvel, F. Fanimarvasti, S. Forbes, A. McBain, J. M. Gardiner, G. D. Brown and S. Freeman, Chem. Commun., 2014, 50, 5000
DOI: 10.1039/C3CC49678C

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