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. 1969 Nov;100(2):977–984. doi: 10.1128/jb.100.2.977-984.1969

Biosynthesis of the Actinomycin Chromophore: Incorporation of 3-Hydroxy-4-Methylanthranilic Acid into Actinomycins by Streptomyces antibioticus

Ellis E Golub a,1, Martha A Ward a, Jonathan S Nishimura a,2
PMCID: PMC250184  PMID: 4187701

Abstract

Actinomycin synthesis by washed mycelia of Streptomyces antibioticus has been conducted in the presence of 3-hydroxy-4-methylanthranilate-(carboxyl-14C). Incorporation of this compound into actinomycins has been observed, which constitutes further evidence that 3-hydroxy-4-methylanthranilate is an intermediate in actinomycin biosynthesis. The position of the incorporated label has been determined to be within the actinomycin chromophore, and the label appears to be equally distributed between both halves of the chromophore. Incidental to these findings was the observation that the 14C-labeled actinomycins were subject to rapid reabsorption by the organism with actinomycin V taken up preferentially to actinomycin IV.

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Selected References

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

  1. FOLCH J., LEES M., SLOANE STANLEY G. H. A simple method for the isolation and purification of total lipides from animal tissues. J Biol Chem. 1957 May;226(1):497–509. [PubMed] [Google Scholar]
  2. GOSS W. A., KATZ E. Actinomycin formation by Streptomyces cultures. Appl Microbiol. 1957 Mar;5(2):95–102. doi: 10.1128/am.5.2.95-102.1957. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. KATZ E., PIENTA P. Decomposition of actinomycin by a soil organism. Science. 1957 Aug 30;126(3270):402–403. doi: 10.1126/science.126.3270.402. [DOI] [PubMed] [Google Scholar]
  4. KATZ E., PIENTA P., SIVAK A. The role of nutrition in the synthesis of actinomycin. Appl Microbiol. 1958 Jul;6(4):236–241. doi: 10.1128/am.6.4.236-241.1958. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. KATZ E., WEISSBACH H. Biosynthesis of the actinomycin chromophore; enzymatic conversion of 4-methyl-3-hydroxyanthranilic acid to actinocin. J Biol Chem. 1962 Mar;237:882–886. [PubMed] [Google Scholar]
  6. KATZ E., WEISSBACH H. Incorporation of C14-labeled amino acids into actinomycin and protein by Streptomyces antibioticus. J Biol Chem. 1963 Feb;238:666–675. [PubMed] [Google Scholar]
  7. KATZ E., WISE M., WEISSBACH H. ACTINOMYCIN BIOSYNTHESIS. DIFFERENTIAL EFFECT OF CHLORAMPHENICOL ON PROTEIN AND PEPTIDE ANTIBIOTIC SYNTHESIS. J Biol Chem. 1965 Jul;240:3071–3078. [PubMed] [Google Scholar]
  8. Katz E., Mauger A. B., Weissbach H. Biosynthesis of highly labeled actinomycins. Mol Pharmacol. 1965 Jul;1(1):107–109. [PubMed] [Google Scholar]
  9. Nishimura J. S., Bowers W. F. Evidence for the incorporation of L-thiazolidine-4-carboxylate into actinomycins by Streptomyces antibioticus. Biochem Biophys Res Commun. 1967 Sep 7;28(5):665–670. doi: 10.1016/0006-291x(67)90366-x. [DOI] [PubMed] [Google Scholar]
  10. Perlman D., Mauger A. B., Weissbach H. Microbial metabolism of actinomycins and other heterodetic antibiotic peptides. Biochem Biophys Res Commun. 1966 Aug 23;24(4):513–518. doi: 10.1016/0006-291x(66)90349-4. [DOI] [PubMed] [Google Scholar]
  11. SIVAK A., MELONI M. L., NOBILI F., KATZ E. Biosynthesis of the actinomycin chromophore. Studies with DL-[7alpha-14C] tryptophan and L-[Me-14C] methionine. Biochim Biophys Acta. 1962 Feb 26;57:283–289. doi: 10.1016/0006-3002(62)91121-6. [DOI] [PubMed] [Google Scholar]
  12. WEISSBACH H., KATZ E. Studies on the biosynthesis of actinomycin: enzymic synthesis of the phenoxazone chromophore. J Biol Chem. 1961 Mar;236:PC16–PC18. [PubMed] [Google Scholar]
  13. WEISSBACH H., REDFIELD B., BEAVEN V., KATZ E. 4-METHYL-3-HYDROXYANTHRANILIC ACID, AN INTERMEDIATE IN ACTINOMYCIN BIOSYNTHESIS. Biochem Biophys Res Commun. 1965 May 3;19:524–530. doi: 10.1016/0006-291x(65)90157-9. [DOI] [PubMed] [Google Scholar]
  14. Waldman A. A., Nishimura J. S. Differential effects of cis-3-methylproline and trans-3-methylproline on actinomycin synthesis in Streptomyces antibioticus. J Biol Chem. 1968 Apr 25;243(8):1833–1838. [PubMed] [Google Scholar]
  15. Weissbach H., Redfield B. G., Beaven V., Katz E. Actinomycin synthesis in washed cells of Streptomyces antibioticus. J Biol Chem. 1965 Nov;240(11):4377–4381. [PubMed] [Google Scholar]

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