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. 2009 Sep;5(9):625-7.
doi: 10.1038/nchembio.189. Epub 2009 Jul 5.

Bacillithiol is an antioxidant thiol produced in Bacilli

Gerald L Newton  1 , Mamta Rawat, James J La Clair, Vishnu Karthik Jothivasan, Tanya Budiarto, Chris J Hamilton, Al Claiborne, John D Helmann, Robert C Fahey
Affiliations

Bacillithiol is an antioxidant thiol produced in Bacilli

Gerald L Newton et al. Nat Chem Biol. 2009 Sep.

Abstract

Glutathione is a nearly ubiquitous, low-molecular-mass thiol and antioxidant, but it is conspicuously absent from most Gram-positive bacteria. We identify here the structure of bacillithiol, a newly described and abundant thiol produced by Bacillus species, Staphylococcus aureus and Deinococcus radiodurans. Bacillithiol is the alpha-anomeric glycoside of L-cysteinyl-D-glucosamine with L-malic acid and most probably functions as an antioxidant. Bacillithiol, like the structurally similar mycothiol, may serve as a substitute for glutathione.

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Figures

FIG. 1
FIG. 1
The hydrolysis of 8 defines its composition. (a) Hydrolysis of 8 in 5 N HCl at 60°C initially results in the release of l-malic acid (10), as determined enzymatically (top), and production of the transient species U8mB and U9mB (11) (bottom). Further hydrolysis of U8mB and U9mB leads to the release of CySmB (9) and GlcN (4). A representative example of three independent experiments is shown. (b) HPLC analysis of the bimane derivatives from a 4 h hydrolysis sample of 8 (panel 1), and of the bimane derivative of synthetic l-CySmB-d-GlcN (11, panel 2) and d-CySmB-d-GlcN (12, panel 4). Synthetic l-CySmB-d-GlcN was mixed with the 4 h hydrolysis sample and coinjected showing that U8mB and U9mB are α, β anomers of l-CySmB-d-GlcN (panel 3) and not d-CySmB-d-GlcN (panel 4).
FIG. 2
FIG. 2
NMR studies confirm the composition of 8, establish linkage in 8 and define the structure of bacillithiol (13): (a) Structure of 8 and of products from acid hydrolysis of 8; (b) HMBC and gCOSY interactions depicting connectivity within 8 and carbon numbering (Supplementary Figs. 3c, 3d, 3i and 3j); (c) NOE interactions in 8 as identified in ROESY spectra (Supplementary Figs. 3e, 3f and 3g); (d) structure of bacillithiol (13); (e) structure of mycothiol (3); (f) a model depicting a complex of a metal (brown) by bacillithiol: H, white; C, green; N, blue; O, red; and S, yellow.
FIG. 3
FIG. 3
See this image and copyright information in PMC

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