Ozonation products of purine derivatives, the basic structures of antiviral micropollutants

Purine and its nucleobases adenine and guanine are the basic structures of a large group of antiviral agents such as acyclovir and penciclovir. Hence, their ozonation is of interest with regard to wastewater treatment due to the formation of products that could affect the aquatic environment. In this study, the transformation products of the mentioned substances are investigated under different defined reaction conditions in order to gain insight into the ozonation characteristics of this compound class. Results show that examining related molecules significantly improves product screening by compiling known products and analogues leading to comprehensive candidate lists, for the purines with a total number of >120 candidates (including possible duplicates for several purines) of which 49 were detected for the derivatives studied. One product, cyanuric acid, which was previously postulated for adenine, was tentatively confirmed and quantified for the first time for the reaction of purine and adenine with ozone. In addition, two prioritisation approaches are presented to identify the major products that are either formed under specific reaction conditions or are potentially relevant for structurally related pollutants. First, principal component analysis allowed the prioritisation of the products formed according to reaction conditions. In the analysis of guanine and the two antivirals, this approach showed that at neutral and basic pH the 2-imino-5-oxoimidazoline products dominated while at acidic pH either analogues of 5-amino-2,4-imidazolidinedione or 2,4-diamino-1,3-oxazol-5-(2H)-one were abundant. A second approach prioritising common products in the ozonation of all three basic structures revealed the formation of two products that had not been reported before: C4H8O3 and C3H2N2O3, presumably oxalylurea. Both molecules or their analogues may also be formed from related micropollutants. Overall, examining basic structures and exemplary micropollutants in combination was shown to be a worthwhile approach to gain knowledge on the ozonation of a whole range of compounds.