Bacillithiol

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Bacillithiol
7-(beta-D-Glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Identifiers
ChEBI CHEBI:61338 N
ChemSpider 24604693 YesY
Jmol 3D model Interactive image
PubChem 42614123
  • InChI=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 YesY
    Key: UHNHELGKNQMNGF-AOQKXWSCSA-N YesY
  • 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
    Key: UHNHELGKNQMNGF-AOQKXWSCBS
  • C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H](CC(=O)O)C(=O)O)NC(=O)[C@H](CS)N)O)O)O
Properties
C13H22N2O10S
Molar mass 398.39 g/mol
Density 1.629 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Bacillithiol (BSH or Cys-GlcN-mal) is a thiol compound found in Bacillus species.[1] 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,[1] although it was first detected in 2007, as an unidentified thiol in Bacillus anthracis.[2] The naturally occurring free thiol form of bacillithiol has since been synthesised and characterised along with its biosynthetic precursors and its symmetrical disulfide.[3]

Biological role

Bacillithiol appears to participate in the sensing of peroxides by Bacillus,[4] but may also substitute for glutathione, which is the most common intracellular thiol in eukaryotes and some bacteria.[1] Some of the genes involved in the biosynthesis of bacillithiol were identified and characterized in 2010.[5] 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.[5] Furthermore, in vitro kinetic studies have established that bacillithiol is a preferred thiol substrate for the antibiotic resistance enzyme FosB.[3] [6]

See also

References

  1. ↑ 1.0 1.1 1.2 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ 5.0 5.1 Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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