Journal
BIOCHEMISTRY
Volume 48, Issue 46, Pages 11142-11148Publisher
AMER CHEMICAL SOC
DOI: 10.1021/bi901343d
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Funding
- National Science Foundation [CHE-0503984, CHE-0911328]
- National Institutes of Health [I R21 DE016889-01A2]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0911328] Funding Source: National Science Foundation
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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.
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