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 |
Journal | Tetrahedron Letters |
Volume | 35 |
Pagination | 4073-4076 |
Date Published | Jun |
Type of Article | Article |
ISBN Number | 0040-4039 |
Keywords | ACID, 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 |
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