Document Detail

Novel actinomycins formed by biosynthetic incorporation of cis- and trans-4-methylproline.
MedLine Citation:
PMID:  69418     Owner:  NLM     Status:  MEDLINE    
Streptomyces parvulus (Streptomyces parvullus) normally produces actinomycin D; in the presence of cis-4-methylproline, this species synthesizes two additional actinomycins, designated K(1c) and K(2c), in which one and two proline sites, respectively, are occupied by cis-4-methylproline. Analogously, actinomycins K(1t) and K(2t) 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 > K(1t) > K(1c) > K(2t) > K(2c) 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.
E Katz; W K Williams; K T Mason; A B Mauger
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Antimicrobial agents and chemotherapy     Volume:  11     ISSN:  0066-4804     ISO Abbreviation:  Antimicrob. Agents Chemother.     Publication Date:  1977 Jun 
Date Detail:
Created Date:  1977-08-25     Completed Date:  1977-08-25     Revised Date:  2009-11-18    
Medline Journal Info:
Nlm Unique ID:  0315061     Medline TA:  Antimicrob Agents Chemother     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  1056-63     Citation Subset:  IM    
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MeSH Terms
Bacillus subtilis / drug effects
Dactinomycin / biosynthesis*
Proline / analogs & derivatives*,  metabolism
Streptomyces / metabolism*
Reg. No./Substance:
147-85-3/Proline; 50-76-0/Dactinomycin

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