ASSOCIATION OF 6-OXO-PIPERIDINE-2-CARBOXYLIC ACID WITH PENICILLIN V

PRODUCTION IN PENICILLIUM CHRYSOGENUM FERMENTATIONS

Abstract

Analysis of a ¹³C NMR spectrum of a concentrated broth from Penicillium chrysogenum fermentation revealed the presence of penicillin V and 6-oxo-piperidine-2-carboxylic acid (1) as the principal constituents. The latter lactam, identical to an authentic sample prepared by the cyclization of α-aminoadipic acid was present to the extent of 28mol% of penicillin V. The lactam isolated from the broth was nearly racemic, having a slight excess of the L-isomer. This isolation provides further evidence regarding the biosynthetic precursors of the hydrophobic penicillins.