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Journal Article

Ralfuranone thioether production by the plant pathogen Ralstonia solanacearum

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Citation

Pauly, J., Spiteller, D., Linz, J., Jacobs, J., Allen, C., Nett, M., et al. (2013). Ralfuranone thioether production by the plant pathogen Ralstonia solanacearum. ChemBioChem: A European Journal of Chemical Biology, 14, 2169-2178. doi:10.1002/cbic.201300364.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-A4C0-1
Abstract
Ralfuranones are aryl-substituted furanone secondary metabolites of the Gram-negative plant pathogen Ralstonia solanacearum. New sulfur-containing ralfuranone derivatives were identified, including the methyl thioether-containing ralfuranone D. Isotopic labeling in vivo, as well as headspace analyses of volatiles from R. solanacearum liquid cultures, established a mechanism for the transfer of an intact methylthio group from l-methionine or a-keto-g-methylthiobutyric acid. The methylthio acceptor molecule ralfuranone I, a previously postulated biosynthetic intermediate in ralfuranone biosynthesis, was isolated and characterized by NMR. The highly reactive Michael acceptor system of this intermediate readily reacts with various thiols, including glutathione.