1887

Abstract

The quinoxaline chromophores of the antibiotics produced by are derived from tryptophan. Protoplasts of this organism made novel products when they were incubated with -5-fluorotryptophan or -6-fluorotryptophan. When added to batch cultures of the organism. -5-fluorotryptophan. at concentrations as low as 10 μm, inhibited both mycelial growth and triostin production, but gave rise to novel products. These have been characterized, using fast atom bombardment mass spectrometry, as novel triostins in which one or both of the quinoxaline rings contain an atom of fluorine. The chromatographic properties of the triostins arising from the incorporation of -5-fluorotryptophan are very similar to those of triostins containing chlorine or bromine at position 6 of the quinoxaline ring; they are clearly different from those having a chlorine atom at position 7. Accordingly, it is suggested that the carbon atom at position 5 of the indole ring of tryptophan ends up at position 6 of the quinoxaline ring system in triostins A and C.

Loading

Article metrics loading...

/content/journal/micro/10.1099/00221287-131-3-561
1985-03-01
2024-04-25
Loading full text...

Full text loading...

/deliver/fulltext/micro/131/3/mic-131-3-561.html?itemId=/content/journal/micro/10.1099/00221287-131-3-561&mimeType=html&fmt=ahah

References

  1. Cornish A., Fox K. R., Waring M. J. 1983a; Preparation and DNA-binding properties of substituted triostin antibiotics. Antimicrobial Agents and Chemotherapy 23:221–231
    [Google Scholar]
  2. Cornish A., Waring M. J., Nolan R. D. 1983b; Conversion of triostins to quinomycins by proto-plasts of Streptomvces echinatus . Journal of Antibiotics 36:1664–1670
    [Google Scholar]
  3. Gorman M., Hamill R. L., Elander R. P., Mabe J. 1968; Preparation of substituted phenyl pyrroles through the metabolism of tryptophan analogues. Biochemical and Biophysical Research Communications 31:294–298
    [Google Scholar]
  4. Katagiri K. 1972; Method for producing triostin. US Patent no. 3647631
    [Google Scholar]
  5. Katagiri K., Yoshida T., Sato K. 1975; Quinoxaline antibiotics. In Antibiotics III. Mechanism of Action of Antimicrobial and Antitumour Agents234–251 Berlin: Springer-Verlag;
    [Google Scholar]
  6. Keller V., Kleinkauf H. 1977; Studies of the biosynthesis of actinomycin in protoplasts from Streptomvces antibioticus . Archives of Biochemistry and Biophysics 184:111–124
    [Google Scholar]
  7. Kuroya M., Ishida N., Katagiri K., Shoji J., Yoshida T., Mayama M., Sato K., Matsuura S., Niinomi Y., Shiratori O. 1961; Studies on quinoxaline antibiotics. I. General properties and the producing strains. Journal of Antibiotics A14:324–329
    [Google Scholar]
  8. Otsuka H., Shoji J. 1965; The structure of triostin C. Tetrahedron 21:2931–2938
    [Google Scholar]
  9. Reid D. G., Doddrell D. M., Williams D. H., Fox K. R. 1984; A 15N nuclear magnetic resonance study of the biosynthesis of quinoxaline antibiotics. Biochimica et biophysica acta 798:111–114
    [Google Scholar]
  10. Santikarn S., Hammond S. J., Williams D. H., Cornish A., Waring M. J. 1983; Characterization of novel antibiotics of the triostin group by fast atom bombardment mass spectrometry. Journal of Antibiotics 36:362–364
    [Google Scholar]
  11. Shirling E. B., Gottlieb D. 1966; Methods for characterization of Streptomvces species. International Journal of Systematic Bacteriology 16:313–340
    [Google Scholar]
  12. Still W. C., Khan M., Mitra A. 1978; Rapid chromatographic technique for preparative separations with moderate resolution. Journal of Organic Chemistry 43:2923–2925
    [Google Scholar]
  13. Yoshida T., Katagiri K. 1967; Influence of iso-leucine upon quinomycin biosynthesis. Journal of Bacteriology 93:1327–1331
    [Google Scholar]
  14. Yoshida T., Katagiri K. 1969; Biosynthesis of the quinoxaline antibiotic, triostin, by Streptomyces S-2-210L. Biochemistry 8:2645–2651
    [Google Scholar]
  15. Yoshida T., Kimura Y., Katagiri K. 1968; Novel quinomycins. Biosynthetic replacement of the chromophores. Journal of Antibiotics 21:465–467
    [Google Scholar]
  16. Yoshida T., Kimura Y., Katagiri K. 1970; The biosynthesis of the quinoxaline antibiotic, triostin, by Streptomyces s-2-210L. On the role of quinoxaline-2-carboxylic acid. In Progress in Antimicrobial and Anticancer Chemotherapy 21160–1165 Tokyo: University of Tokyo Press;
    [Google Scholar]
  17. Waring M. J. 1979; Echinomycin, triostin and related antibiotics. In Antibiotics V, Part II. Mechanism of Action of Antimicrobial and Antitumour Agents234–251 Berlin: Springer-Verlag;
    [Google Scholar]
  18. Werner R. G., Demain A. L. 1981; Directed bio-synthesis of new indolmycins. Journal of Antibiotics 34:551–554
    [Google Scholar]
http://instance.metastore.ingenta.com/content/journal/micro/10.1099/00221287-131-3-561
Loading
/content/journal/micro/10.1099/00221287-131-3-561
Loading

Data & Media loading...

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error