Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer |
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| Authors: | Manikandan Kadirvel William T. Stimpson Souad Moumene-Afifi Biljana Arsic Nicola Glynn Nigel Halliday Paul Williams Peter Gilbert Andrew J. McBain Sally Freeman John M. Gardiner |
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| Affiliation: | 1. School of Pharmacy and Pharmaceutical Sciences, University of Manchester, Manchester M13 9PT, UK;2. School of Chemistry and Manchester Interdisciplinary Biocentre, University of Manchester, Manchester M1 7DN, UK;3. School of Molecular Medical Sciences, University of Nottingham, University Park, Nottingham NG7 2RD, UK |
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| Abstract: | The autoinducer (4S)-4,5-dihydroxypentane-2,3-dione ((S)-DPD, AI-2) facilitates chemical communication, termed ‘quorum sensing’, amongst a wide range of bacteria, The synthesis of (S)-DPD is challenging in part due to its instability. Herein we report a novel synthesis of (S)-DPD via (2S)-2,3-O-isopropylidene glyceraldehyde, through Wittig, dihydroxylation and oxidation reactions, with a complimentary asymmetric synthesis to a key precursor. Its enantiomer (R)-DPD, was prepared from d-mannitol via (2R)-2,3-O-isopropylideneglyceraldehyde. The synthesized enantiomers of DPD have AI-2 bioluminescence-inducing properties in the Vibrio harveyi BB170 strain. |
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