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• W2053971044 abstract "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." @default.
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• W2053971044 date "2001-02-01" @default.
• W2053971044 modified "2023-10-03" @default.
• W2053971044 title "A new inhibitor design strategy for carboxypeptidase A as exemplified by N -(2-chloroethyl)- N -methylphenylalanine" @default.
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• W2053971044 doi "https://doi.org/10.1016/s0968-0896(00)00239-x" @default.
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