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  Insect-associated bacteria assemble the antifungal butenolide gladiofungin by non-canonical polyketide chain termination

Niehs, S. P., Kumpfmueller, J., Dose, B., Little, R. F., Ishida, K., Florez, L. V., et al. (2020). Insect-associated bacteria assemble the antifungal butenolide gladiofungin by non-canonical polyketide chain termination. Angewandte Chemie International Edition, 59(51), 23122-23126. doi:10.1002/anie.202005711.

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https://doi.org/10.1002/anie.202005711 (Publisher version)
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 Creators:
Niehs, Sarah P., Author
Kumpfmueller, Jana, Author
Dose, Benjamin, Author
Little, Rory F., Author
Ishida, Keishi, Author
Florez, Laura V., Author
Kaltenpoth, Martin1, Author              
Hertweck, Christian, Author
Affiliations:
1External Organizations, ou_persistent22              

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Free keywords: NATURAL-PRODUCTS; BIOSYNTHESIS; LACTIMIDOMYCIN; ENDOPHYTES; SYMBIONTS; INSIGHTS; SYSTEMSChemistry; antifungal compounds; biosynthesis; genome mining; natural products; polyketides;
 Abstract: Genome mining of one of the protective symbionts (Burkholderia gladioli) of the invasive beetleLagria villosarevealed a cryptic gene cluster that codes for the biosynthesis of a novel antifungal polyketide with a glutarimide pharmacophore. Targeted gene inactivation, metabolic profiling, and bioassays led to the discovery of the gladiofungins as previously-overlooked components of the antimicrobial armory of the beetle symbiont, which are highly active against the entomopathogenic fungusPurpureocillium lilacinum. By mutational analyses, isotope labeling, and computational analyses of the modular polyketide synthase, we found that the rare butenolide moiety of gladiofungins derives from an unprecedented polyketide chain termination reaction involving a glycerol-derived C3 building block. The key role of an A-factor synthase (AfsA)-like offloading domain was corroborated by CRISPR-Cas-mediated gene editing, which facilitated precise excision within a PKS domain.

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Language(s): eng - English
 Dates: 2020
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: -
 Identifiers: DOI: 10.1002/anie.202005711
Other: KAL112
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 59 (51) Sequence Number: - Start / End Page: 23122 - 23126 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851