2-(4-Amino-4-carboxybutyl)aziridine-2-carboxylic acid. A potent irreversible inhibitor of diaminopimelic acid epimerase. Spontaneous formation from .alpha.-(halomethyl)diaminopimelic acids
- 1 August 1990
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 33 (8) , 2157-2162
- https://doi.org/10.1021/jm00170a018
Abstract
2-(4-Amino-4-carboxybutyl)aziridine-2-carboxylic acid (3) (aziridino-DAP) was identified as the product of spontaneous hydrolysis of .alpha.-(halomethyl)diaminopimelic acids (.alpha.-halomethyl-DAPs) 2a-c. Under physiological conditions, 3 is an extremely potent irreversible inhibitor of the bacterial enzyme diaminopimelic acid epimerase (DAP-epimerase; EC 5.1.1.7). This unusual mode of action of an .alpha.-halomethyl amino acid with a non-pyridoxal enzyme is investigated. Synthesis and characterization of 2a-c and 3, kinetics of spontaneous formation of 3 from .alpha.-halomethyl-DAPs, and kinetics of enzyme inhibition by both 3 and by .alpha.-halomethyl-DAPs are reported.This publication has 8 references indexed in Scilit:
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