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An expeditious synthesis of DPD and boron binding studies
Martin F Semmelhack1, Shawn R Campagna, Michael J Federle
1Departments of Chemistry and Molecular Biology, Princeton University, Princeton, NJ 08544, USA. mfshack@princeton.edu
Abstract:
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]
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