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  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., 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.

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Item Permalink: https://hdl.handle.net/21.11116/0000-000B-3ED7-E Version Permalink: https://hdl.handle.net/21.11116/0000-0010-3987-6
Genre: Journal Article

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Locator:
https://doi.org/10.1002/anie.202206106 (Publisher version)
Description:
Verlagsversion
OA-Status:
Hybrid

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 Creators:
Shi, Y.-M.1, Author           
Crames, J. J.2, Author           
Czech, L., Author
Bozhüyük, K. A. J.2, Author           
Shi, Y.-N.2, Author           
Hirschmann, M., Author
Lamberth, S., Author
Claus, P.3, Author           
Paczia, N.3, Author                 
Ruckert, C., Author
Kalinowski, J., Author
Bange, G.4, Author                 
Bode, H. B.2, 5, 6, 7, Author                 
Affiliations:
1Department of Natural Products in Organismic Interactions, Max Planck Institute for Terrestrial Microbiology, Max Planck Society, ou_3266281              
2Natural Product Function and Engineering, Department of Natural Products in Organismic Interactions, Max Planck Institute for Terrestrial Microbiology, Max Planck Society, ou_3266308              
3Core Facility Metabolomics and small Molecules Mass Spectrometry, Max Planck Institute for Terrestrial Microbiology, Max Planck Society, ou_3266267              
4Max Planck Fellow Molecular Physiology of Microbes, Max Planck Institute for Terrestrial Microbiology, Max Planck Society, ou_3321791              
5Senckenberg Gesellschaft für Naturforschung, Frankfurt, ou_persistent22              
6Molecular Biotechnology, Department of Biosciences, Goethe University Frankfurt, Frankfurt, Germany, External Organizations, ou_421891              
7Chemical Biology, Department of Chemistry, Philipps University Marburg, Marburg, Germany, ou_persistent22              

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Free keywords: Natural products biosynthesis heterocycles non-proteinogenic amino acids non-ribosomal peptide synthetase
 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.

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Language(s): eng - English
 Dates: 2022-10-06
 Publication Status: Issued
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: Other: 36198080
DOI: 10.1002/anie.202206106
ISSN: 1521-3773 (Electronic)1433-7851 (Linking)
 Degree: -

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Project name : LOEWE Centre for Translational Biodiversity Genomics (LOEWE TBG)
Grant ID : -
Funding program : Landes-Offensive zur Entwicklung Wissenschaftlich-ökonomischer Exzellenz (LOEWE)
Funding organization : State of Hesse
Project name : ERC advanced grant SYNPEP
Grant ID : 835108
Funding program : Horizon 2020 (H2020)
Funding organization : European Research Council (EC)
Project name : Open Access
Grant ID : -
Funding program : -
Funding organization : Project DEAL

Source 1

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Title: Angewandte Chemie, International Edition in English
  Abbreviation : Angew. Chem., Int. Ed. Engl.
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 61 (51) Sequence Number: e202206106 Start / End Page: - Identifier: ISSN: 0570-0833
CoNE: https://pure.mpg.de/cone/journals/resource/0570-0833