1887

Abstract

In the presence of -adenosyl--methionine, cell-free extracts of sp. C5, ATCC 29050, ATCC 31913 and ATCC 31276 -methylated carminomycin and 13-dihydrocarminomycin to daunomycin and 13-dihydrodaunomycin, respectively. With the corresponding aglycones, carminomycinone and 13-dihydrocarminomycinone, as substrates, no methylated products were detected. Other 4-hydroxyanthracyclines such as aklavin and aclacinomycin A, and 4-hydroxyanthracyclinones such as ɛ-rhodomycinone and aklavinone, were not substrates for the 4--methyltransferase. These reaction specificities indicate that glycosylation of the anthracyclinone molecule must occur before 4--methylation, which means that 4--methylation of carminomycin is probably the terminal step in the biosynthesis of daunomycin, and that daunomycinone is not an intermediate in the pathway.

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1990-09-01
2022-01-23
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References

  1. Arcamone F., Cassinelli G., Fantini G., Grein A., Orezzi P., Pol C., Spalla C. 1969; Adriamycin, 14-hydroxydaunomycin, a new antitumour antibiotic from S. peucetius var. caesius. Biotechnology and Bioengineering 11:1101–1110
    [Google Scholar]
  2. Blumauerová M., Jizba J., Stajner K., Vanĕk Z. 1979a; Effect of dl-ethionine on the biosynthesis of anthracyclines in Streptomyces coeruleorubidus. Biotechnology Letters 1:471–476
    [Google Scholar]
  3. Blumauerová M., Královcová E., Hoštálek Z., Vanĕk Z. 1979b; Intra- and interspecific cosynthetic activity of mutants of Streptomyces coeruleorubidus and Streptomyces galilaeus impaired in the biosynthesis of anthracyclines. Folia Microbiologica 24:128–135
    [Google Scholar]
  4. Blumauerova M., Královcová E., Matĕjů J., Jizba J., Vanĕk Z. 1979c; Biotransformation of anthracyclinones in Streptomyces coeruleorubidus and Streptomyces galilaeus. Folia Microbiologica 24:117–127
    [Google Scholar]
  5. Brazhnikova M. G., Abarsky V. B., Ponomarenko V. I., Potapova N. P. A. 1974; Physical and chemical characteristics and structure of carminomycin, a new antitumor antibiotic. Journal of Antibiotics 27:254–259
    [Google Scholar]
  6. Connors N. C., Bartel P. L., Strohl W. R. 1990; Biosynthesis of anthracyclines: enzymic conversion of aklanonic acid to aklavinone and ε-rhodomycinone by anthracycline-producing streptomycetes. Journal of General Microbiology 136:1895–1898
    [Google Scholar]
  7. Crespi-Perellino N., Grein A., Merli S., Minghetti A., Spalla C. 1982; Biosynthetic relationships among daunorubicin, doxorubicin and 13-dihydrodaunorubicin in Streptomyces peucetius. Experientia 38:1455–1456
    [Google Scholar]
  8. Dimarco A., Gaetani M., Dorigotti L., Soldati M., Bellini O. 1964; Daunomycin: a new antibiotic with antitumor activity. Cancer Chemotherapy Reports 38:31–38
    [Google Scholar]
  9. Eckardt K., Wagner C. 1988; Biosynthesis of anthracyclinones. Journal of Basic Microbiology 28:137–144
    [Google Scholar]
  10. Fujiwara A., Hoshino T. 1983; Anthracycline antibiotics. CRC Reviews in Biotechnology 3:133–157
    [Google Scholar]
  11. Marshall V. P. 1985; Microbial transformation of anthracycline antibiotics and analogs. Developments in Industrial Microbiology 26:129–142
    [Google Scholar]
  12. Mcguire J. C., Thomas M. C., Stroshane R. M., Hamilton B. K., White R. J. 1980; Biosynthesis of daunorubicin glycosides: role of ε-rhodomycinone. Antimicrobial Agents and Chemotherapy 18:454–464
    [Google Scholar]
  13. Oki T., Kitamura I., Matsuzawa Y., Shibamoto N., Ogasawara T., Yoshimoto A., Inui T. 1979; Antitumor anthracycline antibiotics, aclacinomycin A and analogs. Journal of Antibiotics 32:801–819
    [Google Scholar]
  14. Strohl W. R., Bartel P. L., Connors N. C., Zhu C. -B., Dosch D. C., Beale J. M. Jr Floss H. G., Stutzman-Engwall K., Otten S. L., Hutchinson C. R. 1989; Biosynthesis of natural and hybrid polyketides by anthracycline producing streptomycetes. In Genetics and Molecular Biology of Industrial Microorganisms pp. 68–84 Hershberger C. L., Queener S. W., Hegeman G. Edited by Washington, DC: American Society for Microbiology;
    [Google Scholar]
  15. Tunac J. B., Graham B. D., Dobson W. E., Lenzini M. D. 1985; Fermentation by a new daunomycin-producing organism, Streptomyces insignis ATCC 31913. Applied and Environmental Microbiology 49:265–268
    [Google Scholar]
  16. Yoshimoto A., Oki T., Takeuchi T., Umezawa H. 1980; Microbial conversion of anthracyclinones to daunomycin by blocked mutants of Streptomyces coeruleorubidus. Journal of Antibiotics 33:1158–1166
    [Google Scholar]
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