Reactivity of Nucleosides Toward Hydroxyl Radicals in Aqueous Solution
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Rate constants for reactions of hydroxyl radicals with nucleosides and related compounds were determined by a p-nitrosodimethylaniline method. The obtained rate constants of nucleosides were found to be generally smaller than the sum of those for free bases and ribose, of which the nucleosides are composed. An attempt was made to explain the reduced reactivity of nucleoside in terms of steric hindrance of reaction sites due to other part of the same molecule. The steric hindrance was estimated by solid angle admitted to the radical attack. The observed reactivity was found to be well interpreted by the calculated reactivity according to the following equation, k_<nucleiside>=f_1<kbase>+f_2<kribose> where f_1 and f_2 are steric factors estimated from the solid angles. Reactivity of nucleic acid bases toward hydroxyl radicals has been studied from the view-point of fundamental understanding of radiation-induced damage in nucleic acids. In the succeeding investigation, nucleosides were chosen as the subject compounds which were expected to give the information as to an effect of ribose moiety on reactivity toward hydroxyl radicals.
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