Abstract
Glutathione is a nearly ubiquitous, low-molecular-mass thiol and antioxidant, but it is conspicuously absent from most Gram-positive bacteria. We identify here the structure of bacillithiol, a newly described and abundant thiol produced by Bacillus species, Staphylococcus aureus and Deinococcus radiodurans. Bacillithiol is the alpha-anomeric glycoside of L-cysteinyl-D-glucosamine with L-malic acid and most probably functions as an antioxidant. Bacillithiol, like the structurally similar mycothiol, may serve as a substitute for glutathione.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Antioxidants / chemistry
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Antioxidants / isolation & purification*
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Antioxidants / pharmacology
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Cysteine / analogs & derivatives*
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Cysteine / chemistry
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Cysteine / isolation & purification
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Cysteine / pharmacology
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Deinococcus / metabolism*
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Glucosamine / analogs & derivatives*
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Glucosamine / chemistry
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Glucosamine / isolation & purification
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Glucosamine / pharmacology
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Glutathione / chemistry
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Glutathione / pharmacology
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Models, Molecular
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Molecular Structure
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Staphylococcus aureus / metabolism*
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Sulfhydryl Compounds / chemistry
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Sulfhydryl Compounds / isolation & purification*
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Sulfhydryl Compounds / pharmacology
Substances
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Antioxidants
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Sulfhydryl Compounds
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bacillithiol
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Glutathione
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Cysteine
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Glucosamine
Associated data
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PubChem-Substance/81049156
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PubChem-Substance/81049157
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PubChem-Substance/81049158
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PubChem-Substance/81049159
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PubChem-Substance/81049160
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PubChem-Substance/81049161
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PubChem-Substance/81049162
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PubChem-Substance/81049163
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PubChem-Substance/81049164
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PubChem-Substance/81049165
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PubChem-Substance/81049166
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PubChem-Substance/81049167
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PubChem-Substance/81049168
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PubChem-Substance/81049169
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PubChem-Substance/81049170