This research project in the Organic and Macromolecular Chemistry Program is designed to provide deeper understanding of how certain key organic compounds are synthesized in plants. Cell-free systems containing specific enzymes will be obtained from various parts of alkaloid-producing plants. The ability of these cell-free extracts to catalyze the transformation of known or suspected intermediates in the biosynthesis of the ultimate alkaloids will be examined. In general, the enzymes will be assayed by the use of specifically labeled (carbon, tritium, and deuterium) substrates, the use of which will facilitate identification of products and transient intermediates. Some transformations which will be studied (with the potential source of the enzymes indicated in parenthesis) are the following: (1) the demethylation of nicotine (Nicotinia glutinosa leaves); (2) cocaine biosynthesis (Erythroxylon coca leaves); (3) phenylalanine conversion to (s)-tropic acid (Danutura innoxia roots); (4) tropinone conversion to tropine (Datura innoxia roots); (5) octanoic acid conversion to 5-oxo-octanoic acid (Conium maculatum leaves); and (6) o-succinyl benzoic acid conversion to shihunine (Dendrobium pierardii stems and leaves).