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Water‐Regulated Mechanisms for Degradation of Pesticides Paraoxon and Parathion by Phosphotriesterase: Insight from QM/MM and MD Simulations

Yuzhuang Fu, Fangfang Fan, Binju Wang, Zexing Cao

2022Chemistry - An Asian Journal12 citationsDOI

Abstract

Abstract The enzymatic degradation of pesticides paraoxon (PON) and parathion (PIN) by phosphotriesterase (PTE) has been investigated by QM/MM calculations and MD simulations. In the PTE‐PON complex, Zn α and Zn β in the active site are five‐ and six‐coordinated, respectively, while both zinc ions are six coordinated with the Zn α ‐bound water molecule (WT1) for the PTE‐PIN system. The hydrolytic reactions for PON and PIN are respectively driven by the nucleophilic attack of the bridging‐OH − and the Zn α ‐bound water molecule on the phosphorus center of substrate, and the two‐step hydrolytic process is predicted to be the rate‐limiting step with the energy spans of 13.8 and 14.4 kcal/mol for PON and PIN, respectively. The computational studies reveal that the presence of the Zn α ‐bound water molecule depends on the structural feature of substrates characterized by P=O and P=S, which determines the hydrolytic mechanism and efficiency for the degradation of organophosphorus pesticides by PTE.

Topics & Concepts

ParaoxonChemistryParathionHydrolysisMoleculePesticideZincParathion methylStereochemistryEnzymeOrganic chemistryBiologyAcetylcholinesteraseAgronomyPesticide and Herbicide Environmental StudiesMetal complexes synthesis and propertiesChemical Reaction Mechanisms
Water‐Regulated Mechanisms for Degradation of Pesticides Paraoxon and Parathion by Phosphotriesterase: Insight from QM/MM and MD Simulations | Litcius