THE SYNTHESIS AND STABILITY OF AZIRIDINO-GLUTAMATE, AN IRREVERSIBLE INHIBITOR OF GLUTAMATE RACEMASE

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