Theoretical insights into catalysis by phosphonoacetaldehyde hydrolase

Phosphonatase catalyses P–C bond cleavage in phosphonoacetaldehyde molecules. According to the experimental results this reaction is initiated by Schiff base formation, which facilitates nucleophilic attack on phosphorus. In this paper a preliminary theoretical description of Schiff base formation, P–C bond cleavage and phosphate release is presented, based on quantum chemical calculations at the DFT level of theory, which is probably the first theoretical study of a reaction catalyzed by phosphonatase. Findings from these calculations support the mechanism of imine formation reported in the literature and show that different pathways of phosphonyl transfer can be applied in the active site of phosphonatase.