(2S,3R)- and (2S,3S)-[1-14C,3-3H] phenylalanine were fed in separate experiments to Daturainnoxia plants. The distribution of isotopes in the resultant labeled hyoscyamine and scopolamine indicates that the biosynthesis of the acid moiety of these ester alkaloids, namely (S)-tropic acid, involves the migration of the carboxyl group of phenylalanine to its prochiral C-3 position with retention of configuration.
Enzymology of oxidation of tropic acid to phenylacetic acid in metabolism of atropine by Pseudomonas sp. strain AT3.
