A Novel Stereospecific Synthesis of 14C Labeled 1-Glutamic Acid

Autor: Wurz, R. E. M., Kepner, R. E., Webb, A. D.
Zdroj: Preparative Biochemistry & Biotechnology; January 1989, Vol. 19 Issue: 3 p209-215, 7p
Abstrakt: A stereospecific synthesis of 4-14C-l-glutamic acid was completed in five steps from sodium 2-14C-acetate. The morpholine derived enamine of ethyl pyruvate was reacted with ethyl 2-14C-bromoacetate to give after hydrolysis diethyl 4-14C-2-oxoglutarate. The 2-oxoglutarate was reacted with hydroxylamine hydrochloride to give diethyl 4-14C-2-hydroxyiminoglutarate which was then reduced with a LiAlH4, (-)-N-methylephedrine and 3,5-dimethylphenol mixture to give 4-14C-1-glutamic acid. The 4-14C-1-glutamic acid was used in investigations into the biosynthesis of gamma-lactones in sherries.
Databáze: Supplemental Index