A novel stereospecific synthesis of 14C labeled 1-glutamic acid.
A stereospecific synthesis of 4-14C-1-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.
Wurz
R E
RE
Department of Chemistry, University of California, Davis 95616.
Kepner
R E
RE
Webb
A D
AD
D002250:Carbon Radioisotopes; D005971:Glutamates / Q000138:chemical synthesis*; D018698:Glutamic Acid; D008968:Molecular Conformation
D002250:Carbon Radioisotopes; D005971:Glutamates; D018698:Glutamic Acid