Complementary oxidation of agrochemicals and intermediates by class I and II unspecific peroxygenases

Abstract

Selective oxidation reactions can be a useful tool in the generation of metabolites of bioactive compounds for analytical and toxicology studies. In this study, we show that a range of commonly encountered agrochemicals and synthetic intermediates can be selectively oxidised to form valuable precursors and metabolite compounds using the complementary activities of class I and class II unspecific peroxygenases (UPOs) on preparative scale, permitting full product characterisation. In this way, several UPO-mediated biotransformations of agrochemically relevant intermediates have been uncovered; these include the hydroxylation of phenylureas and isoxazolidinones and the N-dealkylation of triazines. Hence, the herbicide clomazone was hydroxylated by the class I artUPO to give 5-hydroxyclomazone in 27% isolated yield, but was not transformed by the class II UPO rAaeUPO-PaDa-I-H. However, the class II UPO could be used to transform isoproturon to give the hydroxylated product 2-hydroxy-IPU with 57% isolated yield.