Impact of the epoxide hydrolase EphD on the metabolism of mycolic acids in mycobacteria

The Journal of Biological Chemistry
Jan MadackiJana Korduláková

Abstract

Mycolic acids are the hallmark of the cell envelope in mycobacteria, which include the important human pathogens Mycobacterium tuberculosis and Mycobacterium leprae Mycolic acids are very long C60-C90 α-alkyl β-hydroxy fatty acids having a variety of functional groups on their hydrocarbon chain that define several mycolate types. Mycobacteria also produce an unusually large number of putative epoxide hydrolases, but the physiological functions of these enzymes are still unclear. Here, we report that the mycobacterial epoxide hydrolase EphD is involved in mycolic acid metabolism. We found that orthologs of EphD from M. tuberculosis and M. smegmatis are functional epoxide hydrolases, cleaving a lipophilic substrate, 9,10-cis-epoxystearic acid, in vitro and forming a vicinal diol. The results of EphD overproduction in M. smegmatis and M. bovis BCG Δhma strains producing epoxymycolic acids indicated that EphD is involved in the metabolism of these forms of mycolates in both fast- and slow-growing mycobacteria. Moreover, using MALDI-TOF-MS and 1H NMR spectroscopy of mycolic acids and lipids isolated from EphD-overproducing M. smegmatis, we identified new oxygenated mycolic acid species that accumulated during epoxymycolate depletion...Continue Reading

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Citations

Oct 19, 2019·International Microbiology : the Official Journal of the Spanish Society for Microbiology·Sharda SharmaZeeshan Fatima
Nov 15, 2018·Molecular Biology Reports·Gabriel S de OliveiraFelipe S Chambergo
Sep 18, 2020·Science Advances·Alexander M JustenLaura L Kiessling
Oct 8, 2020·Scientific Reports·Eike C SchulzMatthias Wilmanns
Feb 17, 2019·International Journal of Biological Macromolecules·Gabriel S de OliveiraFelipe S Chambergo
Apr 4, 2021·International Journal of Molecular Sciences·Jan MadackiJana Korduláková
Dec 14, 2018·Infection, Genetics and Evolution : Journal of Molecular Epidemiology and Evolutionary Genetics in Infectious Diseases·Jan MadackiRoland Brosch
Jul 9, 2021·Current Research in Structural Biology·Noor M TaherDean R Madden

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