Abstract
Electrophilic halogenating agents, including hypohalous acids and haloamines, oxidize free methionine and the N-terminal methionines of peptides and proteins (e.g., Met-1 of anti-inflammatory peptide 1 and ubiquitin) to produce dehydromethionine (a five-membered isothiazolidinium heterocycle). Amide derivatives of methionine are oxidized to the corresponding sulfoxide derivatives under the same reaction conditions (e.g., Met-3 of anti-inflammatory peptide 1). Other biological oxidants, including hydrogen peroxide and peroxynitrite, also produce only the corresponding sulfoxides. Hypothiocyanite does not react with methionine residues. We suggest that dehydromethionine may be a useful biomarker for the myeloperoxidase-induced oxidative stress associated with many inflammatory diseases.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Biomarkers / analysis
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Biomarkers / chemistry
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Glutathione / analogs & derivatives
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Glutathione / chemistry
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Glutathione Disulfide / chemistry
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Hydrogen Peroxide / chemistry
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Hypochlorous Acid / chemistry*
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Magnetic Resonance Spectroscopy
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Methionine / analogs & derivatives
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Methionine / chemistry*
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Models, Biological
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Models, Chemical
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Neutrophils / enzymology
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Neutrophils / metabolism*
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Oxidants / chemistry
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Oxidation-Reduction
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Oxidative Stress*
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Peptide Fragments / chemistry
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Peroxidase / metabolism
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Proteins / chemistry*
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Spectrometry, Mass, Electrospray Ionization
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Sulfones / chemistry
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Thiazoles / analysis
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Thiazoles / chemistry*
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Ubiquitin / chemistry
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Uteroglobin / chemistry
Substances
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Biomarkers
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Oxidants
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Peptide Fragments
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Proteins
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Sulfones
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Thiazoles
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Ubiquitin
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glutathione sulfonamide
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antiflammin P1
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dehydromethionine
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Hypochlorous Acid
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Uteroglobin
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Methionine
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Hydrogen Peroxide
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Peroxidase
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Glutathione
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Glutathione Disulfide
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methionine sulfoxide