|Title||THE SYNTHESIS AND STABILITY OF AZIRIDINO-GLUTAMATE, AN IRREVERSIBLE INHIBITOR OF GLUTAMATE RACEMASE|
|Publication Type||Journal Article|
|Year of Publication||1994|
|Authors||Tanner, ME, Miao, SC|
|Type of Article||Article|
|Keywords||ACID, EPIMERASE, ESCHERICHIA-COLI, MECHANISM, PEDIOCOCCUS-PENTOSACEUS|
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 with a half life of 4 minutes. Aziridino-glutamate was shown to irreversibly inactivate glutamate racemase by alkylating an active site cysteine 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 denaturing conditions.
|URL||<Go to ISI>://A1994NR71600007|