PMID: 7930837Oct 1, 1994

Addition of e-aq and H atoms to hypoxanthine and inosine and the reactions of alpha-hydroxyalkyl radicals with purines. A pulse radiolysis and product analysis study

International Journal of Radiation Biology
C T AravindakumarC von Sonntag

Abstract

The reactions of hydrated electrons e-aq with hypoxanthine and inosine were followed using pulse radiolysis methods. In a neutral solution the electron adduct of inosine is immediately protonated at the heteroatoms of the purine ring by water (k > 2.5 x 10(6)s-1) to give In(N,O-H).. These N,O-protonated intermediates have a single absorption maximum at 300 nm. In basic solution the protonation of the electron adduct of inosine by water leads to other intermediate products with an absorption maximum at 350 nm. These intermediates are believed to be the C-protonated electron adducts of inosine (In(N,O-H).). In (N,O-H). and In(C-H). differ strongly in their ability to reduce p-nitroacetophenone (PNAP). In(N,O-H). are strong reductants and reduce PNAP quantitatively to PNAP.-. Based on the pH dependence of PNAP.- yields, two types of tautomers of In(C-H). could be distinguished. One of the tautomers can reduce PNAP, albeit with slower rate than In(N,O-H)., the other tautomer has no reducing properties. The latter is the one with the higher pKa and therefore thermodynamically more stable. The absorption spectrum of the intermediates produced in the reaction of e-aq with hypoxanthine at neutral pH is very similar to that of In(N,O-H)...Continue Reading

References

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Related Concepts

4-nitroacetophenone
Acetophenones
Fast Electrons
Free Radicals
Hydrogen
Hypoxanthines
Inosine
Oxidation-Reduction
Protons
Pulse Radiolysis

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