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pubmed-article:11748004pubmed:abstractTextp-Azidophenyl phosphate (I) has been exposed to ultraviolet light (lambda=313 nm) in aqueous solution with or without Lys. Analysis of the photoproducts by means of UV-VIS, IR, (1)H, (13)C and (31)P NMR spectroscopy has revealed that under irradiation of I inorganic phosphate (P(i)) is released, and p-benzoquinone monoimine (II) and p-benzoquinone (III) have appeared. The electrophilic nature of the intermediate results in a high tendency to react with lysine molecules, whereas the reaction with water is less favourable when I is irradiated in the presence of Lys. The product formed in this case is a phosphoramidate whose structure has been tentatively supported by (31)P NMR spectroscopy. These results imply that a p-azidophenyl phosphate is a highly potent aryl nitrene-precursor, which can be transformed easily into p-benzoquinone monoimine and is able to phosphorylate nucleophilic groups of amino acids. This finding is of great importance for the discussions about the chemical nature of protein photomodification products when p-azidophenyl phosphate derivatives are used as modifying reagents.lld:pubmed
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pubmed-article:11748004pubmed:authorpubmed-author:GodovikovaT...lld:pubmed
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pubmed-article:11748004pubmed:authorpubmed-author:AlekseyevP...lld:pubmed
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pubmed-article:11748004pubmed:pagination39-46lld:pubmed
pubmed-article:11748004pubmed:dateRevised2007-7-23lld:pubmed
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pubmed-article:11748004pubmed:year2001lld:pubmed
pubmed-article:11748004pubmed:articleTitlep-Azidophenyl phosphate is a photoactivatable phosphorylating reagent and p-benzoquinone monoimine precursor.lld:pubmed
pubmed-article:11748004pubmed:affiliationNovosibirsk Institute of Bioorganic Chemistry, Siberian Division of the Russian Academy of Sciences, Academica Lavrentyeva av. 8, Novosibirsk, 630090, Russia.lld:pubmed
pubmed-article:11748004pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:11748004pubmed:publicationTypeResearch Support, Non-U.S. Gov'tlld:pubmed