Ralfuranone Thioether Production by the Plant Pathogen Ralstonia solanacearum

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2013
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Pauly, Julia
Linz, Jeanine
Jacobs, Jonathan
Allen, Caitilyn
Nett, Markus
Hoffmeister, Dirk
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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 α-keto-γ-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.

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570 Biowissenschaften, Biologie
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Ralstonia solanacearum, biosynthesis, natural products, ralfuranones, thioethers
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ISO 690PAULY, Julia, Dieter SPITELLER, Jeanine LINZ, Jonathan JACOBS, Caitilyn ALLEN, Markus NETT, Dirk HOFFMEISTER, 2013. Ralfuranone Thioether Production by the Plant Pathogen Ralstonia solanacearum. In: ChemBioChem. 2013, 14(16), pp. 2169-2178. ISSN 1439-4227. eISSN 1439-7633. Available under: doi: 10.1002/cbic.201300364
BibTex
@article{Pauly2013-11-04Ralfu-25172,
  year={2013},
  doi={10.1002/cbic.201300364},
  title={Ralfuranone Thioether Production by the Plant Pathogen Ralstonia solanacearum},
  number={16},
  volume={14},
  issn={1439-4227},
  journal={ChemBioChem},
  pages={2169--2178},
  author={Pauly, Julia and Spiteller, Dieter and Linz, Jeanine and Jacobs, Jonathan and Allen, Caitilyn and Nett, Markus and Hoffmeister, Dirk}
}
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