The Synthesis and Stability of Aziridino-glutamate, an Irreversible Inhibitor of Glutamate Racemase

Article abstract of DOI:10.1016/S0040-4039(00)73115-7

Aziridino-glutamate (2-(2-carboxyethyl)aziridine-2-carboxylic acid, (+/-)4 was synthesized by heating α-fluoromethylglutamate in base.In neutral solution, 4 was shown to cyclize to the γ-lactone 5 with a half life of 4 minutes.Aziridino-glutamate was shown to irreversibily inactivate glutamate racemase by alkylating an active site cystein residue.Electrospray mass spectrometry was used to establish that a covalent bond had formed and that this bond protects one the enzyme's two cysteine residues from reacting with iodoacetate under denaturing conditions.