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]

[1]  B. Bassler,et al.  Boron binding with the quorum sensing signal AI-2 and analogues. , 2004, Organic letters.

[2]  Kim R Hardie,et al.  LuxS: its role in central metabolism and the in vitro synthesis of 4-hydroxy-5-methyl-3(2H)-furanone. , 2002, Microbiology.

[3]  M. Surette,et al.  The LuxS family of bacterial autoinducers: biosynthesis of a novel quorum‐sensing signal molecule , 2001, Molecular microbiology.

[4]  Jenn-jong Young,et al.  Amberlyst-15-catalyzed intramolecular SN2′ oxaspirocyclization of tertiary allylic alcohols , 2000 .

[5]  B. Bassler,et al.  Structural identification of a bacterial quorum-sensing signal containing boron , 2002, Nature.

[6]  A. Dickson.  Thermodynamics of the dissociation of boric acid in synthetic seawater from 273.15 to 318.15 K , 1990 .

[7]  B. Bassler,et al.  Interspecies communication in bacteria. , 2003, The Journal of clinical investigation.

[8]  John O. Edwards,et al.  Polyol Complexes and Structure of the Benzeneboronate Ion , 1959 .

[9]  Kim D Janda,et al.  Synthesis and biological validation of a ubiquitous quorum-sensing molecule. , 2004, Angewandte Chemie.

[10]  J. C. Slaughter,et al.  The naturally occurring furanones: formation and function from pheromone to food. , 2007 .

[11]  D. Pei,et al.  Catalytic mechanism of S-ribosylhomocysteinase (LuxS): direct observation of ketone intermediates by 13C NMR spectroscopy. , 2003, Journal of the American Chemical Society.

[12]  C. Schmid,et al.  2,3-O-(3-Pentylidene)-D-glyceraldehyde and 2,3-O-(3-Pentylidene)-L-glyceraldehyde: Convenient Glyceraldehyde Surrogates Obtained via a Novel Periodate-Based Oxdation System , 1992 .

[13]  Joop A. Peters,et al.  Studies on borate esters II: Structure and stability of borate esters of polyhydroxycarboxylates and related polyols in aqueous alkaline media as studied by 11B NMR , 1985 .

[14]  Shawn R Campagna,et al.  Salmonella typhimurium recognizes a chemically distinct form of the bacterial quorum-sensing signal AI-2. , 2004, Molecular cell.

[15]  D. Seebach,et al.  Note on the Preparation of 1,2‐Diketones from Acetylenes , 1988 .

[16]  J. Yoshida,et al.  Total synthesis of symbioramide, a novel Ca2+-ATPase activator from Symbiodinium sp , 1992 .

[17]  Binghe Wang,et al.  A detailed examination of boronic acid–diol complexation , 2002 .