Bacillithiol

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title: "Bacillithiol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["thiols", "propionamides", "dicarboxylic-acids", "hexosamines"] topic_path: "general/thiols" source: "https://en.wikipedia.org/wiki/Bacillithiol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 460421310 | Name = Bacillithiol | Reference = | ImageFile = Bacillithiol structure.svg | ImageSize = 200px | ImageName = Structure of bacillithiol | IUPACName = (2S)-2-[2-(L-Cysteinamido)-2-deoxy-α-D-glucopyranosyloxy]butanedioic acid | SystematicName = (2S)-2-({(2R,3R,4R,5S,6R)-3-[(2R)-2-Amino-3-sulfanylpropanamido]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl}oxy)butanedioic acid | OtherNames = | Section1 = {{Chembox Identifiers | CASNo_Ref = | CASNo = 1184928-91-3 | Abbreviations = BSH, Cys-GlcN-mal | ChEBI_Ref = | ChEBI = 61338 | PubChem = 42614123 | ChemSpiderID_Ref = | ChemSpiderID = 24604693 | SMILES = C([C@@H]1C@HO)O | InChI = 1/C13H22N2O10S/c14-4(3-26)11(21)15-8-10(20)9(19)6(2-16)25-13(8)24-5(12(22)23)1-7(17)18/h4-6,8-10,13,16,19-20,26H,1-3,14H2,(H,15,21)(H,17,18)(H,22,23)/t4-,5-,6+,8+,9+,10+,13-/m0/s1 | InChIKey = UHNHELGKNQMNGF-AOQKXWSCBS | StdInChI_Ref = | StdInChI = 1S/C13H22N2O10S/c14-4(3-26)11(21)15-8-10(20)9(19)6(2-16)25-13(8)24-5(12(22)23)1-7(17)18/h4-6,8-10,13,16,19-20,26H,1-3,14H2,(H,15,21)(H,17,18)(H,22,23)/t4-,5-,6+,8+,9+,10+,13-/m0/s1 | StdInChIKey_Ref = | StdInChIKey = UHNHELGKNQMNGF-AOQKXWSCSA-N | Section2 = {{Chembox Properties | Formula = C13H22N2O10S | MolarMass = 398.39 g/mol | MeltingPt = | Density = 1.629 g/mL | Section3 = | Section4 = | Section5 = | Section6 =

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 | pmid = 19578333 | pmc = 3510479

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

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 | journal = Proceedings of the National Academy of Sciences | last1 = Lee | 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 | doi-access = free

Biosynthesis

Bacillithiol is produced via the enzymes BshA, BshB, and BshC. BshA replaces the UDP group on UDP-N-acetylglucosamine with an L-malyl group. BshB then removes the acetyl group. L-Cysteine is added to the resulting free amine, which completes the biosynthesis of the molecule. The cysteine-adding step is assumed to be carried out by the enzyme BshC on the basis of genetic knockout studies, but the activity of BshC has not been observed in vitro.

References

References

  1. (July 2011). "Chemical and Chemoenzymatic Syntheses of Bacillithiol: A Unique Low-Molecular-Weight Thiol amongst Low G + C Gram-Positive Bacteria". Angew. Chem. Int. Ed..
  2. (April 2010). "Biosynthesis and functions of bacillithiol, a major low-molecular-weight thiol in Bacilli". Proc. Natl. Acad. Sci. U.S.A..
  3. (July 2013). "Mechanistic studies of FosB: a divalent-metal-dependent bacillithiol-S-transferase that mediates fosfomycin resistance in Staphylococcus aureus". Biochem. J..
  5. (January 20, 2015). "X-ray Crystallographic Structure of BshC, a Unique Enzyme Involved in Bacillithiol Biosynthesis". Biochemistry.

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thiolspropionamidesdicarboxylic-acidshexosamines