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Bacillithiol

|Section2={{Chembox Properties | Formula = C13H22N2O10S | MolarMass = 398.39 g/mol | MeltingPt = | Density = 1.629 g/mL }} }} Bacillithiol (BSH or Cys-GlcN-mal) is a thiol compound found in Bacillus species.{{Cite journal | doi = 10.1038/nchembio.189 | issn = 1552-4450 | last1 = Newton | volume = 5 | issue = 9 | first1 = G. L. | pages = 625–627 | last2 = Rawat | first2 = M. | last3 = La Clair | first3 = J. J. | last4 = Jothivasan | first4 = V. K. | last5 = Budiarto | first5 = T. | last6 = Hamilton | first6 = C. J. | last7 = Claiborne | first7 = A. | last8 = Helmann | first8 = J. D. | last9 = Fahey | first9 = R. C. | title = Bacillithiol is an antioxidant thiol produced in Bacilli | journal = Nature Chemical Biology | year = 2009 | url = http://www.nature.com/nchembio/journal/v5/n9/full/nchembio.189.html | pmid = 19578333 | pmc = 3510479 }} It is likely involved in maintaining cellular redox balance and plays a role in microbial resistance to the antibiotic fosfomycin.

Structure

Chemically, it is a glycoside formed between L-cysteinyl-D-glucosamine and malic acid. It was isolated and identified (as its bacillithiol-S- bimane derivative) in 2009 from Staphylococcus aureus and Deinococcus radiodurans, although it was first detected in 2007, as an unidentified thiol in Bacillus anthracis.{{Cite journal| first1 = I. | last2 = Parsonage | first2 = D. | last4 = Newton | last3 = Paige | last5 = Fahey | first3 = C. | first4 = L. | last7 = Jackowski | last8 = Mallett | first5 = C. | last1 = Nicely | last9 = Claiborne | first6 = R. | last6 = Leonardi | first7 = S. | first8 = C. | first9 = A. | title = STRUCTURE OF THE TYPE III PANTOTHENATE KINASE FROM Bacillus anthracis AT 2.0 Å RESOLUTION: IMPLICATIONS FOR COENZYME A-DEPENDENT REDOX BIOLOGY, | journal = Biochemistry | volume = 46 | issue = 11 | pages = 3234–3245 | date=Mar 2007 | issn = 0006-2960 | pmid = 17323930 | pmc = 2613803 | doi = 10.1021/bi062299p }} The naturally occurring free thiol form of bacillithiol has since been synthesised and characterised along with its biosynthetic precursors and its symmetrical disulfide.

Biological role

Bacillithiol appears to participate in the sensing of peroxides by Bacillus,{{Cite journal| first1 = W. | last2 = Soonsanga | last3 = Helmann | first2 = S. | first3 = D. | title = A complex thiolate switch regulates the Bacillus subtilis organic peroxide sensor OhrR | format = Free full text | journal = Proceedings of the National Academy of Sciences | last1 = Lee | url = http://www.pnas.org/cgi/pmidlookup?view=long&pmid=17502599 | volume = 104 | issue = 21 | pages = 8743–8748 | date=May 2007 | issn = 0027-8424 | pmid = 17502599 | pmc = 1885573 | doi = 10.1073/pnas.0702081104 | bibcode = 2007PNAS..104.8743L }} but may also substitute for glutathione, which is the most common intracellular thiol in eukaryotes and some bacteria. Some of the genes involved in the biosynthesis of bacillithiol were identified and characterized in 2010. Bacteria engineered to be deficient in bacillithiol demonstrated increased sensitivity to various electrophilic xenobiotic compounds, including the antibiotic fosfomycin, suggesting that in these organisms the mechanism of fosfomycin resistance relies on the presence of bacillithiol. Furthermore, in vitro kinetic studies have established that bacillithiol is a preferred thiol substrate for the antibiotic resistance enzyme FosB.

See also

References

"green air" © 2007 - Ingo Malchow, Webdesign Neustrelitz
This article based upon the http://en.wikipedia.org/wiki/Bacillithiol, the free encyclopaedia Wikipedia and is licensed under the GNU Free Documentation License.
Further informations available on the list of authors and history: http://en.wikipedia.org/w/index.php?title=Bacillithiol&action=history
presented by: Ingo Malchow, Mirower Bogen 22, 17235 Neustrelitz, Germany