Characterization of a Copper-Chelating Natural Product from the Methanotroph Methylosinus sp. LW3
- 12 September 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Biochemistry
- Vol. 60 (38), 2845-2850
- https://doi.org/10.1021/acs.biochem.1c00443
Abstract
Methanobactins (Mbns) are ribosomally produced, post-translationally modified peptidic natural products that bind copper with high affinity. Methanotrophic bacteria use Mbns to acquire copper needed for enzymatic methane oxidation. Despite the presence of Mbn operons in a range of methanotroph and other bacterial genomes, few Mbns have been isolated and structurally characterized. Here we report the isolation of a novel Mbn from the methanotroph Methylosinus (Ms.) sp. LW3. Mass spectrometric and nuclear magnetic resonance spectroscopic data indicate that this Mbn, the largest characterized to date, consists of a 13-amino acid backbone modified to include pyrazinedione/oxazolone rings and neighboring thioamide groups derived from cysteine residues. The pyrazinedione ring is more stable to acid hydrolysis than the oxazolone ring and likely protects the Mbn from degradation. The structure corresponds exactly to that predicted on the basis of the Ms. sp. LW3 Mbn operon content, providing support for the proposed role of an uncharacterized biosynthetic enzyme, MbnF, and expanding the diversity of known Mbns.Keywords
Funding Information
- National Institute of General Medical Sciences (F32 GM131665, P41 GM108569, R35 GM118035)
- National Science Foundation
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