An expeditious synthesis of DPD and boron binding studies.
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]
Semmelhack
Martin F
MF
Departments of Chemistry and Molecular Biology, Princeton University, Princeton, NJ 08544, USA. mfshack@princeton.edu
Campagna
Shawn R
SR
Federle
Michael J
MJ
Bassler
Bonnie L
BL
D018407:Bacterial Physiological Phenomena; D001665:Binding Sites; D001895:Boron; D007659:Ketones / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010420:Pentanes / Q000138:chemical synthesis*; D015398:Signal Transduction; D014733:Vibrio / Q000502:physiology
D007659:Ketones; D010420:Pentanes; D001895:Boron