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. 1977 Jun;11(6):1056–1063. doi: 10.1128/aac.11.6.1056

Novel Actinomycins Formed by Biosynthetic Incorporation of cis- and trans-4-Methylproline

E Katz *, W K Williams 1, K T Mason 1, A B Mauger 1
PMCID: PMC352128  PMID: 69418

Abstract

Streptomyces parvulus (Streptomyces parvullus) normally produces actinomycin D; in the presence of cis-4-methylproline, this species synthesizes two additional actinomycins, designated K1c and K2c, in which one and two proline sites, respectively, are occupied by cis-4-methylproline. Analogously, actinomycins K1t and K2t are formed in the presence of trans-4-methylproline. Both mixtures were separated chromatographically, and the four novel actinomycins were obtained in crystalline form. Their biological activities were compared with that of actinomycin D in respect to inhibition of ribonucleic acid, deoxyribonucleic acid, and protein synthesis and antimicrobial potency. In all cases examined, the order of activity D > K1t > K1c > K2t > K2c was observed, and the same sequence prevailed in a spectroscopic measure of their binding to deoxyribonucleic acid. In addition, proton nuclear magnetic resonance studies revealed that the replacement of proline by cis-4-methylproline alters the conformation of the antibiotic molecule.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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