Skip to main content
Antimicrobial Agents and Chemotherapy logoLink to Antimicrobial Agents and Chemotherapy
. 1979 Jan;15(1):42–45. doi: 10.1128/aac.15.1.42

Pyrrolo(1,4)benzodiazepine Antitumor Antibiotics: Biosynthetic Studies on the Conversion of Tryptophan to the Anthranilic Acid Moieties of Sibiromycin and Tomaymycin

Laurence H Hurley 1, Chandrachuranand Gairola 1,
PMCID: PMC352597  PMID: 581831

Abstract

Biosynthetic intermediates between tryptophan and the anthranilate moieties of tomaymycin and sibiromycin have been suggested, based upon a combination of feeding experiments with either carbon-14-labeled substrates or competition experiments between radiolabeled tryptophan and unlabeled intermediates. In the case of sibiromycin and tomaymycin, substitution of the aromatic ring most likely takes place at the kynurenine stage. Feeding experiments with the anthramycin culture were inconclusive, most likely because of the cell impermeability.

Full text

PDF
43

Selected References

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

  1. Hurley L. H., Gairola C., Das N. V. Pyrrolo[1,4]benzodiazepine antibiotics. Biosynthesis of the antitumor antibiotic 11-demethyltomaymycin and its biologically inactive metabolite oxotomaymycin by Streptomyces achromogenes. Biochemistry. 1976 Aug 24;15(17):3760–3769. doi: 10.1021/bi00662a019. [DOI] [PubMed] [Google Scholar]
  2. Hurley L. H. Pyrrolo(1,4)benzodiazepine antitumor antibiotics. Comparative aspects of anthramycin, tomaymycin and sibiromycin. J Antibiot (Tokyo) 1977 May;30(5):349–370. doi: 10.7164/antibiotics.30.349. [DOI] [PubMed] [Google Scholar]
  3. Hurley L. H., Zmijewski M., Chang C. J. Biosynthesis of anthramycin. Determination of the labeling pattern by the use of radioactive and stable isotope techniques. J Am Chem Soc. 1975 Jul 23;97(15):4372–4378. doi: 10.1021/ja00848a040. [DOI] [PubMed] [Google Scholar]
  4. Perlman D., Otani S., Perlman K. L., Walker J. E. 3-Hydroxy-4-methylkynurenine as an intermediate in actinomycin biosynthesis. J Antibiot (Tokyo) 1973 May;26(5):289–296. doi: 10.7164/antibiotics.26.289. [DOI] [PubMed] [Google Scholar]

Articles from Antimicrobial Agents and Chemotherapy are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES