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

TitleTHE SYNTHESIS AND STABILITY OF AZIRIDINO-GLUTAMATE, AN IRREVERSIBLE INHIBITOR OF GLUTAMATE RACEMASE
Publication TypeJournal Article
Year of Publication1994
AuthorsTanner, ME, Miao, SC
JournalTetrahedron Letters
Volume35
Pagination4073-4076
Date PublishedJun
Type of ArticleArticle
ISBN Number0040-4039
KeywordsACID, EPIMERASE, ESCHERICHIA-COLI, MECHANISM, PEDIOCOCCUS-PENTOSACEUS
Abstract

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