Biosynthesis of Sinapigladioside,an Antifungal Isothiocyanate from Burkholderia Symbionts |
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Authors: | Benjamin Dose Dr. Sarah P. Niehs Dr. Kirstin Scherlach Sophie Shahda Dr. Laura V. Flórez Prof. Dr. Martin Kaltenpoth Prof. Dr. Christian Hertweck |
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Affiliation: | 1. Department of Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology, HKI, Beutenbergstr. 11a, 07745 Jena, Germany;2. Department for Evolutionary Ecology, Institute of Organismic and Molecular Evolution, Johannes Gutenberg University, Johann-Joachim-Becher-Weg 13, 55128 Mainz, Germany |
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Abstract: | Sinapigladioside is a rare isothiocyanate-bearing natural product from beetle-associated bacteria (Burkholderia gladioli) that might protect beetle offspring against entomopathogenic fungi. The biosynthetic origin of sinapigladioside has been elusive, and little is known about bacterial isothiocyanate biosynthesis in general. On the basis of stable-isotope labeling, bioinformatics, and mutagenesis, we identified the sinapigladioside biosynthesis gene cluster in the symbiont and found that an isonitrile synthase plays a key role in the biosynthetic pathway. Genome mining and network analyses indicate that related gene clusters are distributed across various bacterial phyla including producers of both nitriles and isothiocyanates. Our findings support a model for bacterial isothiocyanate biosynthesis by sulfur transfer into isonitrile precursors. |
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Keywords: | biosynthesis Burkholderia genome mining isothiocyanate natural products |
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