338462-77-4

Upstream product

• 159090-52-5 (S)-methyl 2-[benzyl(methyl)amino]-3-phenylpropanoate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 2439-60-3 N-methyl-L-phenylalanine methyl ester 
• 338462-76-3 (S)-N-(2-hydroxyethyl)-N-methylphenylalanine methyl ester 
• 66399-75-5 (S)-2-benzylamino-3-phenyl-propionic acid methyl ester 

Relevant academic research and scientific papers

A new inhibitor design strategy for carboxypeptidase A as exemplified by N-(2-Chloroethyl)-N-methylphenylalanine

N-(2-Chloroethyl)-N-methylphenylalanine was designed and synthesized in an optically active form as a novel class of mechanism-based inactivator for carboxypeptidase A (CPA). It was anticipated that the chloroethylamino moiety of the CPA bound inhibitor undergoes an intramolecular SN2 reaction to generate a chemically reactive species (an aziridinium ion) which is expectedly subjected to a nucleophilic attack by the carboxylate of Glu-270, leading to covalent modification of the carboxylate. The irreversible nature of the inhibition of CPA by the inhibitor was supported by the kinetic data: the enzyme lost its enzymic activity in a time-dependent manner in the presence of the inhibitor and the inactivated CPA failed to regain the activity upon dialysis. Interestingly, the (R)-isomer that belongs to the D-series was more potent than its enantiomer.