A novel stereospecific synthesis of sup 14 C labeled 1-glutamic acid

Journal Article · Sat Dec 31 23:00:00 EST 1988 · Preparative Biochemistry; (USA)

DOI:https://doi.org/10.1080/10826068908544911· OSTI ID:6945730

Wurz, R E; Kepner, R E; Webb, A D ^[1]

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1. Univ. of California, Davis (USA)

A stereospecific synthesis of 4-{sup 14}C-1-glutamic acid was completed in five steps from sodium 2-{sup 14}C-acetate. The morpholine derived enamine of ethyl pyruvate was reacted with ethyl 2-{sup 14}C-bromoacetate to give after hydrolysis diethyl 4-{sup 14}C-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-{sup 14}C-1-glutamic acid. The 4-{sup 14}C-1-glutamic acid was used in investigations into the biosynthesis of gamma-lactones in sherries.

• OSTI ID: 6945730
• Journal Information: Preparative Biochemistry; (USA), Journal Name: Preparative Biochemistry; (USA) Vol. 19:3; ISSN PRBCB; ISSN 0032-7484
• Country of Publication: United States
• Language: English

Related Subjects

550201* -- Biochemistry-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
AMINO ACIDS
BIOSYNTHESIS
CARBON 14 COMPOUNDS
CARBOXYLIC ACIDS
CHEMICAL PREPARATION
ESTERS
GLUTAMIC ACID
HETEROCYCLIC COMPOUNDS
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
LACTONES
MOLECULAR STRUCTURE
ORGANIC ACIDS
ORGANIC COMPOUNDS
SYNTHESIS
TRACER TECHNIQUES