Bioorganic and Medicinal Chemistry Letters p. 2625 - 2628 (2010)
Update date:2022-08-04
Topics:
Kadirvel, Manikandan
Stimpson, William T.
Moumene-Afifi, Souad
Arsic, Biljana
Glynn, Nicola
Halliday, Nigel
Williams, Paul
Gilbert, Peter
McBain, Andrew J.
Freeman, Sally
Gardiner, John M.
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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