Ralfuranone Thioether Production by the Plant Pathogen Ralstonia solanacearum
Ralfuranone Thioether Production by the Plant Pathogen Ralstonia solanacearum
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DOI：
10.1002/cbic.201300364
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发表时间：
2013-11
期刊：
影响因子：
3.2
通讯作者：
J. Pauly;Dieter Spiteller;J. Linz;J. Jacobs;C. Allen;M. Nett;D. Hoffmeister
中科院分区：
文献类型：
--
作者：
J. Pauly;Dieter Spiteller;J. Linz;J. Jacobs;C. Allen;M. Nett;D. Hoffmeister
Ralfuranones是革兰氏阴性植物病原体青枯菌（Ralstonia solanacearum）的芳基取代的呋喃酮次级代谢产物。鉴定了新的含硫的ralfuranone衍生物，包括含甲基硫醚的ralfuranone D。采用同位素标记法和顶空分析法对红曲霉挥发物进行了体内分析。青枯菌液体培养物，建立了从L-甲硫氨酸或α-酮基-γ-甲硫基丁酸转移完整甲硫基的机制。甲硫基受体分子ralfuranone I，一个以前假定的生物合成中间体ralfuranone的生物合成，分离和其特征在于通过NMR。该中间体的高反应性迈克尔受体系统容易与各种硫醇反应，包括谷胱甘肽。
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.