Directed biosynthesis of new indolmycins

J Antibiot (Tokyo). 1981 May;34(5):551-4. doi: 10.7164/antibiotics.34.551.


Tryptophan in a concentration of 0.4 microgram/ml increased the production of indolmycin by 37%. The lipophilic character of indolmycin was reduced via directed biosynthesis by substituting the aromatic ring system with a methoxy or hydroxy group in the 5-position of the antibiotic. This substitution was achieved by the addition of the corresponding tryptophan and indole precursors to a growing culture of Streptomyces griseus ATCC 12648. The more hydrophilic indolmycin derivatives displayed a moderate increase in antimicrobial activity as compared to indolmycin, but did not markedly change the Gram-positive/Gram-negative ratio of activity. Thin-layer chromatography and mass spectrometry showed that additives substituted in the 6-position were not incorporated into the molecule. Antibiotic titer was reduced by addition of the modified precursors, especially in the case of the precursors substituted in the 6-position.

MeSH terms

  • Anti-Bacterial Agents / biosynthesis*
  • Bacteria / drug effects
  • Chemical Phenomena
  • Chemistry, Physical
  • Indoles / biosynthesis*
  • Indoles / pharmacology
  • Microbial Sensitivity Tests
  • Streptomyces griseus / metabolism*
  • Time Factors


  • Anti-Bacterial Agents
  • Indoles
  • indolmycin