Characterization of a Copper-Chelating Natural Product from the Methanotroph Methylosinus sp. LW3
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.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:60 |
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| Enthalten in: |
Biochemistry - 60(2021), 38 vom: 28. Sept., Seite 2845-2850 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Park, Yun Ji [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 19.11.2021 Date Revised 29.09.2022 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1021/acs.biochem.1c00443 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM330530941 |
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| 100 | 1 | |a Park, Yun Ji |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Characterization of a Copper-Chelating Natural Product from the Methanotroph Methylosinus sp. LW3 |
| 264 | 1 | |c 2021 | |
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| 500 | |a Date Completed 19.11.2021 | ||
| 500 | |a Date Revised 29.09.2022 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a 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 | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, N.I.H., Extramural | |
| 650 | 4 | |a Research Support, U.S. Gov't, Non-P.H.S. | |
| 650 | 7 | |a Bacterial Proteins |2 NLM | |
| 650 | 7 | |a Biological Products |2 NLM | |
| 650 | 7 | |a Chelating Agents |2 NLM | |
| 650 | 7 | |a Imidazoles |2 NLM | |
| 650 | 7 | |a Oligopeptides |2 NLM | |
| 650 | 7 | |a Peptides |2 NLM | |
| 650 | 7 | |a methanobactin |2 NLM | |
| 650 | 7 | |a Copper |2 NLM | |
| 650 | 7 | |a 789U1901C5 |2 NLM | |
| 650 | 7 | |a Methane |2 NLM | |
| 650 | 7 | |a OP0UW79H66 |2 NLM | |
| 700 | 1 | |a Roberts, Gerri M |e verfasserin |4 aut | |
| 700 | 1 | |a Montaser, Rana |e verfasserin |4 aut | |
| 700 | 1 | |a Kenney, Grace E |e verfasserin |4 aut | |
| 700 | 1 | |a Thomas, Paul M |e verfasserin |4 aut | |
| 700 | 1 | |a Kelleher, Neil L |e verfasserin |4 aut | |
| 700 | 1 | |a Rosenzweig, Amy C |e verfasserin |4 aut | |
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