Abstract
The 53-414 strain of Penicillium chrysogenum was cultured in a defined medium containing glucose, acetate, lactate, and phenylacetic acid as carbon sources and 99.8% deuterium oxide as solvent. Partially deuterated benzylpenicillin was isolated from the culture. The extent of solvent participation in the biosynthesis of the penicillin molecule was determined by analysis of the proton magnetic resonance spectra. Incorporation of deuterium appears almost complete at two positions: the C-3 position of the thiazol-idine ring and the C-6 position of the β-lactam ring. A partial incorporation of deuterium at the C-5 position is also observed. The deuterium atoms in the C-5 and C-6 positions apparently arise during biosynthesis of the amino acid cysteine. The deuterium atom at the C-3 position apparently arises either in the biosynthesis of the amino acid valine or in the closing of the thiazolidine ring.
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