Genome mining enabled by biosynthetic characterization uncovers a class of 
benzoxazolinate-containing natural products in diverse bacteria

Shi, Y.-M.; Crames, J. J.; Czech, L.; Bozhüyük, K. A. J.; Shi, Y.-N.; Hirschmann, M.; Lamberth, S.; Claus, P.; Paczia, N.; Ruckert, C.; Kalinowski, J.; Bange, G.; Bode, H. B.

doi:10.1002/anie.202206106

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Genome mining enabled by biosynthetic characterization uncovers a class of benzoxazolinate-containing natural products in diverse bacteria

MPS-Authors

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Shi, Y.-M.
Department of Natural Products in Organismic Interactions, Max Planck Institute for Terrestrial Microbiology, Max Planck Society;

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Crames, J. J.
Natural Product Function and Engineering, Department of Natural Products in Organismic Interactions, Max Planck Institute for Terrestrial Microbiology, Max Planck Society;

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Bozhüyük, K. A. J.
Natural Product Function and Engineering, Department of Natural Products in Organismic Interactions, Max Planck Institute for Terrestrial Microbiology, Max Planck Society;

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Shi, Y.-N.
Natural Product Function and Engineering, Department of Natural Products in Organismic Interactions, Max Planck Institute for Terrestrial Microbiology, Max Planck Society;

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Claus, P.
Core Facility Metabolomics and small Molecules Mass Spectrometry, Max Planck Institute for Terrestrial Microbiology, Max Planck Society;

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Paczia, N.
Core Facility Metabolomics and small Molecules Mass Spectrometry, Max Planck Institute for Terrestrial Microbiology, Max Planck Society;

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Bange, G.
Max Planck Fellow Molecular Physiology of Microbes, Max Planck Institute for Terrestrial Microbiology, Max Planck Society;

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Bode, H. B.
Natural Product Function and Engineering, Department of Natural Products in Organismic Interactions, Max Planck Institute for Terrestrial Microbiology, Max Planck Society;
Senckenberg Gesellschaft für Naturforschung, Frankfurt;
Molecular Biotechnology, Department of Biosciences, Goethe University Frankfurt, Frankfurt, Germany, External Organizations;
Chemical Biology, Department of Chemistry, Philipps University Marburg, Marburg, Germany;

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https://doi.org/10.1002/anie.202206106
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Citation

Shi, Y.-M., Crames, J. J., Czech, L., Bozhüyük, K. A. J., Shi, Y.-N., Hirschmann, M., et al. (2022). Genome mining enabled by biosynthetic characterization uncovers a class of benzoxazolinate-containing natural products in diverse bacteria. Angewandte Chemie, International Edition in English, 61(51): e202206106. doi:10.1002/anie.202206106.

Cite as: https://hdl.handle.net/21.11116/0000-000B-3ED7-E

Abstract

Benzoxazolinate is a rare bis-heterocyclic moiety that interacts with proteins and DNA and confers extraordinary bioactivities on natural products, such as C-1027. However, the biosynthetic gene responsible for the key cyclization step of benzoxazolinate remains unclear. Here, we show a putative acyl AMP-ligase responsible for the last cyclization step. We then use the enzyme as a probe for genome mining and discover that the orphan benzobactin gene cluster in entomopathogenic bacteria prevails across Proteobacteria and Firmicutes. It turns out that Pseudomonas chlororaphis produces various benzobactins, whose biosyntheses arehighlighted by a synergistic effect of two unclustered genes encoding enzymes on boosting benzobactin production; the formation of non-proteinogenic 2-hydroxymethylserine by a serine hydroxymethyltransferase; and the types I and II NRPS architecture for structural diversity. Our findings reveal the biosynthetic potential of a widespread benzobactin gene cluster.