Metathesis-based synthesis of jasmonate and homojasmonate lactones, candidates for extracellular quorum sensing molecules in Candida albicans

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Su C. Cho, Patrick H. Dussault, Amber D. Lisec, Ellen C. Jensen and Kenneth W. Nickerson


Abstract

Ring-closing metathesis of jasmonate esters is shown to provide a rapid entry to jasmonate lactones. The lactones were investigated as possible quorum sensing molecules for the fungi Candida albicans. Assays demonstrated no effect on fungal morphology at concentrations up to 96 µM.


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