PMID:2197412
| Citation |
Gerhart, F, Higgins, W, Tardif, C and Ducep, JB (1990) 2-(4-Amino-4-carboxybutyl)aziridine-2-carboxylic acid. A potent irreversible inhibitor of diaminopimelic acid epimerase. Spontaneous formation from alpha-(halomethyl)diaminopimelic acids. J. Med. Chem. 33:2157-62 |
|---|---|
| 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. |
| Links | |
| Keywords |
Amino Acid Isomerases; Amino Acids, Diamino; Aziridines/pharmacology; Chemical Phenomena; Chemistry; Diaminopimelic Acid/analogs & derivatives; Escherichia coli/enzymology; Hydrolysis; Isomerases/antagonists & inhibitors; Kinetics; Racemases and Epimerases/antagonists & inhibitors; Thermodynamics |
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