A Modified,High Yield Procedure for the Synthesis of Unlabeled and 14C-Labeled 4-Methylene-DL-glutamic Acid |
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Authors: | G K Powell E E Dekker |
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Institution: | Department of Biological Chemistry , The University of Michigan , Ann Arbor, Michigan, 48109 |
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Abstract: | This paper describes the complete chemical synthesis of 4-methylene-DL-glutamic acid from diethylmalonate, formaldehyde and diethyl acetamidomalonate. The amino acid was obtained pure following ion-exchange chromatography and/or crystallization from hot water in an overall yield of 30% based on the amount of diethylmalonate used. Several physico-chemical characteristics of the synthetic compound were determined, including ir and pmr spectra, chromatography on paper, retention time on an amino acid analyzer, pK values and melting point; all properties cf the synthetic material were found to be identical to those seen with the naturally occurring L-isomer. The procedure for obtaining gram quantities of the unlabeled compound has also been modified for the synthesis of high specific activity (10.6 mCi/nmol) 4-methylene-2-14C]-DL-glutamic acid. |
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