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 x 10(4). This enantioselective result was explained by the fact that the R-isomer of rac-hapten was more immunogenic than the S-isomer.
Shi
Zhen-Dan
ZD
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Yang
Bing-Hui
BH
Zhao
Jing-Jing
JJ
Wu
Yu-Lin
YL
Ji
Yong-Yong
YY
Yeh
Ming
M
D000818:Animals; D000911:Antibodies, Monoclonal / Q000378:metabolism*; D002384:Catalysis; D002478:Cells, Cultured; D006868:Hydrolysis; D007700:Kinetics; D051379:Mice; D008807:Mice, Inbred BALB C; D009288:Naproxen / Q000378:metabolism*; D013057:Spectrum Analysis; D013237:Stereoisomerism
D000911:Antibodies, Monoclonal; D009288:Naproxen