Tetrahedron Letters p. 4073 - 4076 (1994)
Update date:2022-07-29
Topics:
Tanner, Martin E.
Miao, Shichang
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.
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