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Bacillithiol

Bacillithiol
Structure of bacillithiol
Structure of bacillithiol
Names
IUPAC name
(2S)-2-[2-(L-Cysteinamido)-2-deoxy-α-D-glucopyranosyloxy]butanedioic acid
Systematic IUPAC name
(2S)-2-({(2R,3R,4R,5S,6R)-3-[(2R)-2-Amino-3-sulfanylpropanamido]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl}oxy)butanedioic acid
Identifiers
3D model (JSmol)
Abbreviations Cys-GlcN-mal
ChEBI
ChemSpider
  • 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 checkY
    Key: UHNHELGKNQMNGF-AOQKXWSCSA-N checkY
  • 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 checkY☒N ?)

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.

  1. ^ Newton, G. L.; Rawat, M.; La Clair, J. J.; Jothivasan, V. K.; Budiarto, T.; Hamilton, C. J.; Claiborne, A.; Helmann, J. D.; Fahey, R. C. (2009). "Bacillithiol is an antioxidant thiol produced in Bacilli". Nature Chemical Biology. 5 (9): 625–627. doi:10.1038/nchembio.189. ISSN 1552-4450. PMC 3510479. PMID 19578333.

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باسیلیتیول AZB Bacilitiol Spanish باسیلیتیول FA Bacilitiol SH Bacilitiol Serbian

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