Reactivity and synthesis of substituted furanones and a novel approach to optically active derivatives applied in quorum-sensing inhibition bioassays

ORGN 145

Tobias Persson1, John Nielsen1, and Thomas Hjelmgaard2. (1) Department of Chemistry, The Royal Veterinary and Agricultural University, Thorvaldsensvej 40, DK-1871 Frederiksberg C, Denmark, (2) Department of Chemistry, Technical University of Denmark, Kemitorvet, Building 207, Kgs. Lyngby, 2800, Denmark
The richness of furanones as a natural source for finding new biological activities in general and in the quorum sensing system in particular, urged us to involve in reactivity and synthesis of different derivatives. The probable mechanism of action for 4-bromo-5-(bromomethylene)-2(5H)-furanones, a potent quorum sensing inhibitor, was revealed by the reaction with a range of nucleophiles analogous to amino acids. Furthermore, two independent strategies for synthesis of 3- and/or 5-substituted furanones have been utilized. Another simple route on solid phase to obtain combinatorial libraries of optically active furanones is under investigation.