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• W2044463323 abstract "The reactive 1,2-didehydroazepine (cyclic ketenimine) intermediates produced upon photolysis of phenyl azide, 3-hydroxyphenyl azide, 3-methoxyphenyl azide, and 3-nitrophenyl azide in water and in HEPES buffer were studied by laser flash photolysis techniques with UV−vis detection of the transient intermediates. The lifetimes of the 1,2-didehydroazepines were obtained along with the absolute rate constants of their reactions with typical amino acids, nucleosides, and other simple reagents present in a biochemical milieu. The nitro substituent greatly accelerates the bimolecular reactions of the cyclic ketenimines, and the 3-methoxy group greatly decelerates the absolute reactivity of 1,2-didehydroazepines. The intermediate produced by photolysis of 3-hydroxyphenyl azide is much more reactive than the intermediate produced by photolysis of 3-methoxyphenyl azide. We propose that the hydroxyl-substituted 1,2-didehydoazepines rapidly (<10 μs) tautomerize in water to form azepinones and much more rapidly than the corresponding 3-methoxy-substituted cyclic ketenimines undergo hydrolysis. Azepinones react more rapidly with nucleophiles than do methoxy-substituted 1,2-didehydroazepines and are the active species present upon the photolysis of 3-hydroxyphenyl azide in aqueous solution." @default.
• W2044463323 created "2016-06-24" @default.
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• W2044463323 date "2005-12-15" @default.
• W2044463323 modified "2023-10-16" @default.
• W2044463323 title "Lifetimes and Reactivities of Some 1,2-Didehydroazepines Commonly Used in Photoaffinity Labeling Experiments in Aqueous Solutions" @default.
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• W2044463323 doi "https://doi.org/10.1021/bi0516632" @default.
• W2044463323 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/16401083" @default.
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