The Role of 2-Piperidneacetic Acid in the Biosythesis of Lycopodine

Abstract

<p>The role of 2-piperidineacetic acid in the biosynthesis of lycopodine was tested by feeding experiments with β-14C-2-piperidineacetic acid hydrochloride. The compound was synthesized starting from 2-picolylchloride which was treated with K14CN yielding the labeled 2-pyridineacetonitrile. Conversion of the nitrile to the ester was followed by reduction of the pyridine ring and hydrolysis of the ester function. The labeled β-14C-2-piperidineacetic acid was obtained in 60% radiochemical yield. When administered to L. tristachyum, alone or along with radioactive lysine, β-14C-2-piperidineacetic acid showed very low incorporation into lycopodine. The incorporation of lysine into lycopodine showed however that the alkaloid was being synthesized in the plant in the course of the feeding experiments. These results cast doubt on the hypothesis that 2-piperidineacetlc acid is an intermediate on the pathway to lycopodine from lysine.</p>