Acyl Histidines: New N‐Acyl Amides from Legionella pneumophila
Open accessAbstract
Legionella pneumophila, the causative agent of Legionnaires' disease, is a Gram‐negative gammaproteobacterial pathogen that infects and intracellularly replicates in human macrophages and a variety of protozoa. L. pneumophila encodes an orphan biosynthetic gene cluster (BGC) that contains isocyanide‐associated biosynthetic genes and is upregulated during infection. Because isocyanide‐functionalized metabolites are known to harbor invertebrate innate immunosuppressive activities in bacterial pathogen–insect interactions, we used pathway‐targeted molecular networking and tetrazine‐based chemoseletive ligation chemistry to characterize the metabolites from the orphan pathway in L. pneumophila. We also assessed their intracellular growth contributions in an amoeba and in murine bone‐marrow‐derived macrophages. Unexpectedly, two distinct groups of aromatic amino acid‐derived metabolites were identified from the pathway, including a known tyrosine‐derived isocyanide and a family of new N‐acyl‐l‐histidine metabolites.
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The practice of labeling functional groups in uncharacterized NP mixtures using a non-targeted metabolomics approach is uncommon in NP discovery, and there are currently only a few existing examples.
“Although these approaches have been in certain cases efficiently applied for NP discovery, the practice of labeling functional groups in uncharacterized NP mixtures using a non-targeted metabolomics approach is uncommon in NP discovery, and there are currently only a few existing examples.124–128”
From Connecting metabolome and phenotype: recent advances in functional metabolomics tools for the identification of bioactive natural products (2024) · cites this paper as [127]
The Results and Discussion section, “A tetrazine probe identifies an isocyanide metabolite” (page unavailable), describes using a tetrazine probe and LC/MS to detect isocyanide-functionalized metabolites in bacterial cultures. This makes the paper an example of functional-group-based metabolite discovery, but it does not establish that the practice is uncommon or that only a few examples exist. (LLM, conf=0.86)
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References 50 · Cited by 16
- Authors
- Tørring, T., Shames, S. R., Cho, W., Roy, C. R., & Crawford, J. M.
- Affiliations
- Aarhus University (DK)
- Yale University (US)
- Corresponding author
- Crawford, Jason M.
- Venue
- ChemBioChem
- Publisher
- Wiley
- Published
- 2017-03-06
- Volume
- 18
- Issue
- 7
- Pages
- 638-646
- ISSN
- 1439-4227 (ISSN-L)
- 1439-7633
- PMC
- PMC5546091
- OpenAlex
- W2582357119
- Cited by
- 16
- References
- 50
- Citations by year
- 2026: 2 · 2025: 1 · 2024: 3 · 2022: 2 · 2021: 2 · 2019: 4 · 2018: 1 · 2017: 1
- FWCI
- 1.15
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- ChemBioChem (publishedVersion)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- Funders
- National Cancer Institute (1DP2-CA186575)
- National Institute of Allergy and Infectious Diseases (AI041699, AI048770)
- Topics
- Health Sciences › Medicine › Pharmacology › Microbial Natural Products and Biosynthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Endocrinology › Legionella and Acanthamoeba research
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Bacterial biofilms and quorum sensing
- Keywords
- Legionella pneumophila, macrophage infection, amoebae
- MeSH terms
- Amides, Animals, Multigene Family, Histidine, Macrophages, Pyridines, Molecular Probes, Legionella pneumophila, Acanthamoeba castellanii, Mice
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