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Reaction of sulphate radical anion (SO. 4 -) with hydroxy-and methyl-substituted pyrimidines: a pulse radiolysis study

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Abstract

Reactions of sulphate radical anion (SO·4 -) with 4,6-dihydroxy-2-methyl pyrimidine (DHMP), 2,4-dimethyl-6-hydroxy pyrimidine (DMHP), 6-methyl uracil (MU) and 5,6-dimethyl uracil (DMU) have been studied by pulse radiolysis at pH 3 and at pH 10. The transient intermediate spectra were compared with those from the reaction of hydroxyl radical (·OH). It is proposed that SO·4 - produces radical cations of these pyrimidines in the initial stage. These radical cations are short-lived except in the case of DMHP where a relatively longer lived radical cation is proposed to be formed. When there is a hydrogen atom attached to the N(1) or N(3) position, a deprotonation from these sites is highly favored. When there is no hydrogen attached to these sites, deprotonation from a substituted methyl group is favored. At acidic pH, deprotonation from nitrogen is observed for DHMP, MU and DMU. At basic pH, the radical cation reacts with OH- leading to the formation of OH adducts.

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Authors
  1. T. L. Luke
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  2. H. Mohan
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  3. V. M. Manoj
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  4. P. Manoj
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  5. J. P. Mittal
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  6. C. T. Aravindakumar
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Luke, T.L., Mohan, H., Manoj, V.M. et al. Reaction of sulphate radical anion (SO. 4 -) with hydroxy-and methyl-substituted pyrimidines: a pulse radiolysis study. Research on Chemical Intermediates 29, 379–391 (2003). https://doi.org/10.1163/156856703765694327

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