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Comparison of intermediates of tryptophan, tyrosine and their dipeptide induced by UV light and SO.4

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The chemical processes of tryptophan (Trp), tyrosine (Tyr) and a dipeptide Trp-Tyr, which are induced by UV radiation and one-electron oxidation of SO.4, have been investigated in aqueous solution by KrF (248 nm) laser flash photolysis. On the basis of optical studies, the photoionization of Trp and Tyr produces the tryptophan indolyl radical and tyrosine phenoxyl radical, respectively, and these are different from the intermediates resulting from interaction of Trp and Tyr with SO.4. In the case of Trp, SO.4 would attack the indole moiety to produce a C(2)-yl sulphate radical adduct, and Tyr is oxidized to produce mainly the corresponding one-electron oxidized radical, which deprotonates rapidly to form the phenoxyl radical in neutral solution, and a possible sulphate radical adduct. From transient absorption spectra of photoionization of Trp-Tyr, an intramolecular electron transfer, Trp/N.-Tyr → Trp-Tyr/O., has been observed, but there was no observation of the process of one-electron oxidation of Trp-Tyr by SO.4.


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