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

被引：55

作者：

TANNER, ME

MIAO, SC

机构：

[1] Department of Chemistry, University of British Columbia, Vancouver

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 24期

关键词：

D O I：

10.1016/S0040-4039(00)73115-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

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页码：4073 / 4076

页数：4

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