Evidence for the Formation of Ozone (or Ozone-Like Oxidants) by the Reaction of Singlet Oxygen with Amino Acids

Abstract

Antibodies or some amino acids, namely, cysteine, methionine, histidine, and tryptophan, were previously reported to catalyse the conversion of singlet oxygen (1O2) to ozone (O3). The originally proposed mechanism for such biological ozone formation was that antibodies or amino acids catalyse the oxidation of water molecules by singlet oxygen to yield dihydrogen trioxide (HOOOH) as a precursor of ozone and hydrogen peroxide (H2O2). However, because HOOOH readily decomposes to form water and singlet oxygen rather than ozone and hydrogen peroxide, an alternative hypothesis has been proposed; ozone is formed due to the reaction of singlet oxygen with amino acids to form polyoxidic amino acid derivatives as ozone precursors. Evidence in support of the latter hypothesis is presented in this article, in that in the presence of singlet oxygen, methionine sulfoxide (RS(O)CH3), an oxidation product of methionine (RSCH3), was found to promote reactions that can best be attributed to the trioxidic anionic derivative RS+(OOO−)CH3or ozone.