Pyrrolo[1,4]benzodiazepine antibiotics. Biosynthesis of the antitumor antibiotic 11-demethyltomaymycin and its biologically inactive metabolite oxotomaymycin by Streptomyces achromogenes.

@article{Hurley1976Pyrrolo14benzodiazepineAB,
  title={Pyrrolo[1,4]benzodiazepine antibiotics. Biosynthesis of the antitumor antibiotic 11-demethyltomaymycin and its biologically inactive metabolite oxotomaymycin by Streptomyces achromogenes.},
  author={L. Hurley and C. Gairola and N. V. Das},
  journal={Biochemistry},
  year={1976},
  volume={15 17},
  pages={
          3760-9
        }
}
  • L. Hurley, C. Gairola, N. V. Das
  • Published 1976
  • Chemistry, Medicine
  • Biochemistry
    • 11-Demethyltomaymycin, an antitumor antibiotic produced by Streptomyces achromogenes, and its biologically inactive metabolite oxotomaymycin are biosynthesized from L-tyrosine, DL-tryptophan, and L-methionine. The anthranilate part of 11-demethyltomaymycin is derived from tryptophan probably via the kynurenine pathway. The predominant loss of tritium from DL-[5-3H]tryptophan, during its conversion to 11-demethyltomaymycin and oxotomaymycin is interpreted to mean by NIH shift rules, that the… CONTINUE READING
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    References

    SHOWING 1-10 OF 12 REFERENCES
    On the preparation of L-[2,3-3H2]phenylalanine and L-[2,3-3H2]tyrosine
    • 9
    Biosynthesis of dithiadiketopiperazine antibiotics: comparison of possible aromatic amino acid precusors.
    • 16
    Studies on tomaymycin, a new antibiotic. I. Isolation and properties of tomaymycin.
    • 72
    Mode of action of tomaymycin.
    • 23
    • PDF
    The origin of methyl groups of 4'-depropyl-4'-ethyllincomycin (U-21699).
    • 2
    Metabolism of chloramphenicol by the producing organism. Some properties of chloramphenicol hydrolase.
    • 25
    Studies in relation to biosynthesis. Part XLVI. Incorporation of cyclo-L-tryptophyl-L-proline into brevianamide A
    • 36
    The Structures of Tomaymycin and Oxotomaymycin
    • 45
    Biosynthesis of anthramycin. Determination of the labeling pattern by the use of radioactive and stable isotope techniques.
    • 35
    Bioconversion of tyrosine into the propylhygric acid moity of lincomycin.
    • 33