8 Non Enzymatic Transformation of Phenylalanine to Tropic Acid
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It has been previously shown that phenylalanine is a precursor of tropic acid (I) in Datura Stramonium plants. We have found that tropic acid is formed from phenylalanine or its ethyl ester by its chemical deamination with nitrous acid through 1, 2-migration of phenyl group (T. L., 1967, 3007; 1971, 2283, 2287). For the extension of this work, atropine and apoatropine were obtained by the deamination of IV with sodium nitrite in dilute sulfuric acid. When L-phenylalanine was deaminated with sodium nitrite in trifluoroacetic acid, S(-)-tropic acid which shows the same absolute configuration with natural tropic acid, was obtained, on the other hand, the deamination of L-phenylalanine ethyl ester gave antipodal R(+)-tropic acid.
