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Covalent binding of the 13C-labeled skin sensitizers 5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI) to a model peptide and glutathione



Covalent binding of the 13C-labeled skin sensitizers 5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI) to a model peptide and glutathione



Bioorganic & Medicinal Chemistry Letters 14(2): 365-368



The reactivity of 4-[13C]- and 5-[13C]-5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI) towards a model peptide and glutathione was followed by 13C and 1H[13C] NMR spectroscopy. Both molecules were found to react with GSH but in addition MCI was found to react with histidine and lysine to form adducts of a different nature. Reaction with histidine led to stable substitution adducts through an addition-elimination reaction at position 5 while reaction with lysine led to the formation of open adducts of the thioamide or amide type.

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Accession: 048678513

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PMID: 14698160



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Covalent binding of the 13C-labeled skin sensitizers 5-chloro-2-methylisothiazol-3-one and 2-methylisothiazol-3-one to a model peptide and glutathione. Bioorganic & Medicinal Chemistry Letters 14(2): 365-368, 19 January, 2004

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