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Issue 20, 2020
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Structure elucidation of the redox cofactor mycofactocin reveals oligo-glycosylation by MftF

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Abstract

Mycofactocin (MFT) is a redox cofactor belonging to the family of ribosomally synthesized and post-translationally modified peptides (RiPPs) and is involved in alcohol metabolism of mycobacteria including Mycobacterium tuberculosis. A preliminary biosynthetic model had been established by bioinformatics and in vitro studies, while the structure of natural MFT and key biosynthetic steps remained elusive. Here, we report the discovery of glycosylated MFT by 13C-labeling metabolomics and establish a model of its biosynthesis in Mycolicibacterium smegmatis. Extensive structure elucidation including NMR revealed that MFT is decorated with up to nine β-1,4-linked glucose residues including 2-O-methylglucose. Dissection of biosynthetic genes demonstrated that the oligoglycosylation is catalyzed by the glycosyltransferase MftF. Furthermore, we confirm the redox cofactor function of glycosylated MFTs by activity-based metabolic profiling using the carveol dehydrogenase LimC and show that the MFT pool expands during cultivation on ethanol. Our results will guide future studies into the biochemical functions and physiological roles of MFT in bacteria.

Graphical abstract: Structure elucidation of the redox cofactor mycofactocin reveals oligo-glycosylation by MftF

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Supplementary files

Article information


Submitted
26 Feb 2020
Accepted
18 Apr 2020
First published
23 Apr 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 5182-5190
Article type
Edge Article

Structure elucidation of the redox cofactor mycofactocin reveals oligo-glycosylation by MftF

L. Peña-Ortiz, A. P. Graça, H. Guo, D. Braga, T. G. Köllner, L. Regestein, C. Beemelmanns and G. Lackner, Chem. Sci., 2020, 11, 5182
DOI: 10.1039/D0SC01172J

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