bacillithiol

Also known as Cys-GlcN-mal, BSH

Bacillithiol (BSH or Cys-GlcN-mal) is a thiol compound found in Bacillus species. It is likely involved in maintaining cellular redox balance and plays a role in microbial resistance to the antibiotic fosfomycin.

Chemical data

Formula: C13H22N2O10S
Molecular weight: 398.39 g/mol
IUPAC name: (2S)-2-[(2R,3R,4R,5S,6R)-3-[[(2R)-2-amino-3-sulfanylpropanoyl]amino]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanedioic acid

via PubChem

Wikidata facts

Mass: 398.1

Show 3 more facts

chemical formula: C₁₃H₂₂N₂O₁₀S
isomeric SMILES: 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
canonical SMILES: C(C1C(C(C(C(O1)OC(CC(=O)O)C(=O)O)NC(=O)C(CS)N)O)O)O

Sources (1)

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Article

5 sections

Contents

Structure
Biological role
Biosynthesis
See also
References

{{chembox | 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 = | Section2 = | Section3 = | Section4 = | Section5 = | Section6 = }}