An expeditious synthesis of DPD and boron binding studies

Org Lett. 2005 Feb 17;7(4):569-72. doi: 10.1021/ol047695j.


A practical synthesis has been developed for DPD (4,5-dihydroxypentane-2,3-dione), an unstable small molecule that is proposed to be the source of universal signaling agents for quorum sensing in bacteria. The synthesis allows preparation of isotopically labeled DPD and ent-DPD as well as detailed studies of spontaneous binding to borate to give the unusual borate complex 6, the signal for marine bacteria such as Vibrio harveyi. [reaction: see text]

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacterial Physiological Phenomena
  • Binding Sites
  • Boron*
  • Ketones / chemical synthesis
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Pentanes / chemical synthesis*
  • Signal Transduction
  • Vibrio / physiology


  • Ketones
  • Pentanes
  • Boron