Base-promoted reaction of 5-hydroxyuracil derivatives with peroxyl radicals

Org Lett. 2010 Sep 17;12(18):4130-3. doi: 10.1021/ol1017245.

Abstract

Addition of millimolar amounts of a weak base (pyridines) dramatically accelerates the reaction with peroxyl radicals of two biologically relevant uracil derivatives, 5-hydroxyuracil (HU) and 5-hydroxy-6-methyluracil (HMU). This is due to the formation of small amounts of the deprotonated form (pK(a) = 8.1-8.5 in water), which reacts with peroxyl radicals much faster than the parent undissociated form, via formal H-atom transfer from the OH in the 5 position.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Molecular Structure
  • Oxygen / chemistry
  • Peroxides / chemistry*
  • Uracil / analogs & derivatives*
  • Uracil / chemistry

Substances

  • Peroxides
  • 5-hydroxyuracil
  • Uracil
  • Oxygen