Me. Tanner et Sc. Miao, THE SYNTHESIS AND STABILITY OF AZIRIDINO-GLUTAMATE, AN IRREVERSIBLE INHIBITOR OF GLUTAMATE RACEMASE, Tetrahedron letters, 35(24), 1994, pp. 4073-4076
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.