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J Bacteriol. 1968 March; 95(3): 952-958
Copyright © 1968 American Society for Microbiology. All Rights Reserved.

Effect of Structural and Stereochemical Methylproline Isomers on Actinomycin Biosynthesis

Department of Microbiology, Schools of Medicine and Dentistry, Georgetown University, Washington, D.C. 20007
Laboratory of Clinical Biochemistry, National Heart Institute, Bethesda, Maryland 20014

ABSTRACT

The inhibitory effect of methylprolines on actinomycin biosynthesis by Streptomyces antibioticus was studied; the order of effectiveness was 3- >4- >5-methyl-DL-proline. Cis-3-methyl-DL-proline was 14 times more active than the trans isomer. It was also found that 4- and, possibly, 5-methylproline were incorporated into the actinomycin molecule. When 4-methylproline was present, three new actinomycins, representing 50 to 60% of the antibiotic mixture, were synthesized. Growth of the organism may be stimulated at concentrations (0.1 to 1.0 µg per ml) of 3-methylproline that inhibit antibiotic formation, thus providing additional evidence for a different mechanism of actinomycin synthesis from that of protein synthesis. Azetidine-2-carboxylic acid, piperdine-2-carboxylic acid, and hydroxyproline (but not sarcosine) reversed the inhibition due to 3-methylproline.

¹ Present address: Shionogi Research Laboratory, Shionogi and Co., Osaka, Japan.