Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer

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

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2625-2628
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume20
Issue number8
Early online date19 Feb 2010
DOIs
Publication statusPublished - 15 Apr 2010

Keywords

  • AI-2
  • Autoinducer
  • DPD

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer'. Together they form a unique fingerprint.

Cite this