Enantioselective Uptake Determines Degradation Selectivity of Chiral Profenofos in Cupriavidus nantongensis X1T

Organophosphorus insecticides account for approximately 28% of the global commercial insecticide market, while 40% of them are chiral enantiomers. Chiral enantiomers differ largely in their toxicities. Enantiomers that are less active or inactive do not offer the needed efficacy but pollute the environment and cause toxicities to non-target species. Cupriavidus nantongensis X1(T), a recently isolated bacterial strain, could degrade S-profenofos 2.3-fold faster than R-profenofos, while the latter is the active enantiomer potently against pest insects and has greater mammalian safety. The degradation enzyme encoded by opdB was expressed via Escherichia coli and purified. The degradation kinetics of R- and S-profenofos showed that both the purified OpdB and crude enzyme extracts had no enantiomer degradation selectivity, which strongly indicated that the degradation selectivity occurred in the uptake process. Metabolite analyses suggested a novel dealkylation pathway. This is the first report of bacterial selective uptake of organophosphates. Selective degradation of S-profenofos over R-profenofos by the strain X1(T) suggests a concept of co-application of racemic pesticides and degradation-selective bacteria to minimize contamination and non-target toxicity problems.