Enantioselective hydrolysis of naproxen ethyl ester catalyzed by monoclonal antibodies

This report described that a hapten of racemic phosphonate 3 designed as the mimic of the transition state of hydrolysis of naproxen ethyl ester was successfully synthesized from easily available 2-acetyl-6-methoxy-naphthalene 5 . Then BALB/C mice were immunized and one of the monoclonal catalytic antibodies, N116-27, which enantioselectively accelerated the hydrolysis of the R -(−)-naproxen ethyl ester was given. The Michaelis–Menton parameter for the catalyzed reaction was K M =6.67 mM and k cat / k uncat =5.8×10 4 . This enantioselective result was explained by the fact that the R -isomer of rac-hapten was more immunogenic than the S -isomer.