N-methyl-bacillithiol, a Novel Thiol from Anaerobic Bacteria

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Abstract

J. Hiras, S. V. Sharma, V. Raman, R. A. J. Tinson, et al. (mBio 9:e01603-18, 2018, https://doi.org/10.1128/mBio.01603-18) report on the identification of a novel thiol, N-methyl-bacillithiol (N-Me-BSH), in the green sulfur bacterium Chlorobium tepidum. In N-methyl-bacillithiol, the amine of the cysteine is methylated by a novel S-adenosylmethioneine transferase designated N-methyl-bacillithiol synthase A (NmbA). The Hiras et al. study is significant because it is the first report of the presence of N-Me-BSH in anaerobic bacteria.

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High levels of intracellular cysteine promote oxidative DNA damage by driving the fenton reaction.

Sunny Park, James Imlay (2003)

Escherichia coli is generally resistant to H(2)O(2), with >75% of cells surviving a 3-min challenge with 2.5 mM H(2)O(2). However, when cells were cultured with poor sulfur sources and then exposed to cystine, they transiently exhibited a greatly increased susceptibility to H(2)O(2), with <1% surviving the challenge. Cell death was due to an unusually rapid rate of DNA damage, as indicated by their filamentation, a high rate of mutation among the survivors, and DNA lesions by a direct assay. Cell-permeable iron chelators eliminated sensitivity, indicating that intracellular free iron mediated the conversion of H(2)O(2) into a hydroxyl radical, the direct effector of DNA damage. The cystine treatment caused a temporary loss of cysteine homeostasis, with intracellular pools increasing about eightfold. In vitro analysis demonstrated that cysteine reduces ferric iron with exceptional speed. This action permits free iron to redox cycle rapidly in the presence of H(2)O(2), thereby augmenting the rate at which hydroxyl radicals are formed. During routine growth, cells maintain small cysteine pools, and cysteine is not a major contributor to DNA damage. Thus, the homeostatic control of cysteine levels is important in conferring resistance to oxidants. More generally, this study provides a new example of a situation in which the vulnerability of cells to oxidative DNA damage is strongly affected by their physiological state.

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Bacillithiol is an antioxidant thiol produced in Bacilli

Gerald L. Newton, Mamta Rawat, James J. La Clair … (2009)

Glutathione is a nearly ubiquitous low-molecular-weight thiol and antioxidant, although it is conspicuously absent from most Gram-positive bacteria. We identify here the structure of bacillithiol, a novel and abundant thiol produced by Bacillus species, Staphylococcus aureus, and Deinococcus radiodurans. Bacillithiol is the α-anomeric glycoside of l-cysteinyl-d-glucosamine with l-malic acid and likely functions as an antioxidant. Bacillithiol, like structurally similar mycothiol, may serve as a substitute for glutathione.

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Occurrence of glutathione in bacteria.

Lesa Worsham, John W Adams, C. Brown … (1978)

Glutathione and soluble thiol content were examined in a broad spectrum of bacteria. Significant soluble thiol was present in all cases. The thiol compound was glutathione in most of the gram-negative bacteria but not in most of the gram-positive bacteria studied. Glutathione was absent in four anerobes and one microaerophile but was present in a blue-green bacterium. The glutathione content of Escherichia coli increased significantly during transition from exponential to stationary phase.

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Author and article information

Journal

Journal ID (nlm-ta): mBio

Journal ID (iso-abbrev): MBio

Journal ID (hwp): mbio

Journal ID (pmc): mbio

Journal ID (publisher-id): mBio

Title: mBio

Publisher: American Society for Microbiology (1752 N St., N.W., Washington, DC )

ISSN (Electronic): 2150-7511

Publication date (Electronic): 15 January 2019

Publication date Collection: Jan-Feb 2019

Volume: 10

Issue: 1

Electronic Location Identifier: e02634-18

Affiliations

[a ]Division of Biological Sciences, University of California, San Diego, San Diego, California, USA

[b ]Department of Biology, California State University—Fresno, Fresno, California, USA

Author notes

Address correspondence to Mamta Rawat, mrawat@ 123456csufresno.edu .

Article

Publisher ID: mBio02634-18

DOI: 10.1128/mBio.02634-18

PMC ID: 6336425

PubMed ID: 30647158

SO-VID: 453da343-9b58-4071-a769-9203a81fd0c5

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This is an open-access article distributed under the terms of the Creative Commons Attribution 4.0 International license.

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Figures: 1, Tables: 0, Equations: 0, References: 32, Pages: 5, Words: 3067

Funding

Funded by: HHS | National Institutes of Health (NIH), https://doi.org/10.13039/100000002;

Award ID: SC3GM100855

Award Recipient : Mamta Rawat

Funded by: National Science Foundation (NSF), https://doi.org/10.13039/100000001;

Award ID: 1244611

Award Recipient : Mamta Rawat

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cover-date January/February 2019

ScienceOpen disciplines: Life sciences

Keywords: chlorobium,n-methyl-bacillithiol,anaerobes,bacillithiol,glutathione,thiols

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ScienceOpen disciplines: Life sciences

Keywords: chlorobium, n-methyl-bacillithiol, anaerobes, bacillithiol, glutathione, thiols

N-methyl-bacillithiol, a Novel Thiol from Anaerobic Bacteria

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Most cited references 29

High levels of intracellular cysteine promote oxidative DNA damage by driving the fenton reaction.

Bacillithiol is an antioxidant thiol produced in Bacilli

Occurrence of glutathione in bacteria.

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