Crochelins: Siderophores with an Unprecedented Iron‐Chelating Moiety from the Nitrogen‐Fixing Bacterium Azotobacter chroococcum
Abstract
Microbes use siderophores to access essential iron resources in the environment. Over 500 siderophores are known, but they utilize a small set of common moieties to bind iron. Azotobacter chroococcum expresses iron‐rich nitrogenases, with which it reduces N 2. Though an important agricultural inoculant, the structures of its iron‐binding molecules remain unknown. Here, the “chelome” of A. chroococcum is examined using small molecule discovery and bioinformatics. The bacterium produces vibrioferrin and amphibactins as well as a novel family of siderophores, the crochelins. Detailed characterization shows that the most abundant member, crochelin A, binds iron in a hexadentate fashion using a new iron‐chelating γ‐amino acid. Insights into the biosynthesis of crochelins and the mechanism by which iron may be removed upon import of the holo‐siderophore are presented. This work expands the repertoire of iron‐chelating moieties in microbial siderophores.
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Previous techniques for elucidating metal-binding relied on properties of the metal-adduct itself, including metal-specific isotopic signatures, mass defect/Kendrick analysis, or hyperfine splitting isotope patterns.
“Previous techniques for elucidating metal-binding have relied on properties of the metal-adduct itself, including the presence of metal-specific isotopic signatures,87,88 mass defect/Kendrick analysis,89 or analysis of hyperfine splitting isotope patterns.90”
From Connecting metabolome and phenotype: recent advances in functional metabolomics tools for the identification of bioactive natural products (2024) · cites this paper as [88]
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- Authors
- Baars, O., Zhang, X., Gibson, M. I., Stone, A. T., Morel, F. M. M., & Seyedsayamdost, M. R.
- Affiliations
- Princeton University (US)
- Johns Hopkins University (US)
- Corresponding author
- Seyedsayamdost, Mohammad R.
- ORCID
- Venue
- Angewandte Chemie
- Publisher
- Wiley
- Published
- 2017-12-08
- Volume
- 130
- Issue
- 2
- Pages
- 545-550
- ISSN
- 0044-8249 (ISSN-L)
- 1521-3757
- OpenAlex
- W4239234335
- Cited by
- 19
- References
- 22
- Citations by year
- 2026: 4 · 2025: 2 · 2024: 3 · 2023: 2 · 2021: 3 · 2020: 1 · 2019: 2 · 2018: 2
- FWCI
- 0.95
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- Angewandte Chemie (publishedVersion)
- Funders
- Princeton Environmental Institute, Princeton University (PEI Innovation Research Award)
- National Science Foundation (OCE 1315200, EAR 1631814)
- Pew Charitable Trusts (Pew Biomedical Scholars Program)
- Topics
- Health Sciences › Medicine › Pharmacology › Microbial Natural Products and Biosynthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Genetics › Bacterial Genetics and Biotechnology
- Physical Sciences › Energy › Renewable Energy, Sustainability and the Environment › Metalloenzymes and iron-sulfur proteins
- Keywords
- siderophores, Azotobacter chroococcum, iron acquisition, γ-amino acids, siderophore biosynthesis, nitrogen-fixing bacteria
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