Skip to main content
NCBI home page
Antimicrobial Agents and Chemotherapy logoLink to Antimicrobial Agents and Chemotherapy
. 1975 Feb;7(2):208–214. doi: 10.1128/aac.7.2.208

Sequence of Biosynthesis of the Components of the Polyene Macrolides Candidin and Candihexin: Macrolide Aglycones as Intracellular Components

Juan F Martin 1,1, Lloyd E McDaniel 1
PMCID: PMC429105  PMID: 1137372

Abstract

A sequential formation of the single components of the polyene macrolide candidin complex (heptaene) has been found. In addition to the three components occurring in the candidin complex at the end of the fermentation, two other “early” all-trans heptaene components have been characterized. They exist only during the phase of active biosynthesis of candidin. Two of the components of the polyene macrolide candihexin complex (hexaene) that have been described as lacking amino sugar were the only intracellular (mycelium-associated) components observed under conditions in which no extracellular polyene remained attached to the producing cell. The results indicate that glycosylation of the macrolide ring takes place during the secretion process.

Full text

PDF
208

Selected References

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

  1. Bergy M. E., Eble T. E. The filipin complex. Biochemistry. 1968 Feb;7(2):653–659. doi: 10.1021/bi00842a021. [DOI] [PubMed] [Google Scholar]
  2. Dhar M. M., Khan A. W. Formation of antibiotics. Nature. 1971 Sep 17;233(5316):182–184. doi: 10.1038/233182a0. [DOI] [PubMed] [Google Scholar]
  3. Eylar E. H. On the biological role of glycoproteins. J Theor Biol. 1966 Jan;10(1):89–113. doi: 10.1016/0022-5193(66)90179-2. [DOI] [PubMed] [Google Scholar]
  4. Gordon H. W., Schaffner C. P. The effect of polyene macrolides on the prostate gland and canine prostatic hyperplasia. Proc Natl Acad Sci U S A. 1968 Aug;60(4):1201–1208. doi: 10.1073/pnas.60.4.1201. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. HUNG P. P., MARKS C. L., TARDREW P. L. THE BIOSYNTHESIS AND METABOLISM OF ERYTHROMYCINS BY STREPTOMYCES ERYTHREUS. J Biol Chem. 1965 Mar;240:1322–1326. [PubMed] [Google Scholar]
  6. Hamilton-Miller J. M. Chemistry and biology of the polyene macrolide antibiotics. Bacteriol Rev. 1973 Jun;37(2):166–196. [PMC free article] [PubMed] [Google Scholar]
  7. Keshin J. G. Effect of candicidin on the human benign hypertrophied prostate gland. Int Surg. 1973 Feb;58(2):116–122. [PubMed] [Google Scholar]
  8. Liu C. M., McDaniel L. E., Schaffner C. P. Fungimycin, biogenesis of its aromatic moiety. J Antibiot (Tokyo) 1972 Mar;25(3):187–188. doi: 10.7164/antibiotics.25.187. [DOI] [PubMed] [Google Scholar]
  9. Liu C. M., McDaniel L. E., Schaffner C. P. Studies on candicidin biogenesis. J Antibiot (Tokyo) 1972 Feb;25(2):116–121. doi: 10.7164/antibiotics.25.116. [DOI] [PubMed] [Google Scholar]
  10. MCDANIEL L. E., BAILEY E. G., ZIMMERLI A. EFFECT OF OXYGEN SUPPLY RATES ON GROWTH OF ESCHERICHIA COLI. Appl Microbiol. 1965 Jan;13:109–114. doi: 10.1128/am.13.1.109-114.1965. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Manwaring D. G., Rickards R. W., Gaudiano G., Nicolella V. The biosynthesis of the macrolide antibiotic lucensomycin. J Antibiot (Tokyo) 1969 Nov;22(11):545–550. doi: 10.7164/antibiotics.22.545. [DOI] [PubMed] [Google Scholar]
  12. Martin J. F., McDaniel L. E. Isolation, purification and properties of the hexaene macrolides candihexin I and candihexin II. J Antibiot (Tokyo) 1974 Aug;27(8):610–619. doi: 10.7164/antibiotics.27.610. [DOI] [PubMed] [Google Scholar]
  13. Martin J. F., McDaniel L. E. Quantitative thin-layer spectrodensitometric determination of the components of polyene macrolide antibiotice complexes. J Chromatogr. 1975 Jan 29;104(1):151–160. doi: 10.1016/s0021-9673(01)85499-6. [DOI] [PubMed] [Google Scholar]
  14. Martin J. R., Rosenbrook W. Studies on the biosynthesis of the erythromycins. II. Isolation and structure of a biosynthetic intermediate, 6-deoxyerythronolide B. Biochemistry. 1967 Feb;6(2):435–440. doi: 10.1021/bi00854a010. [DOI] [PubMed] [Google Scholar]
  15. McDaniel L. E., Bailey E. G. Liquid nitrogen preservation of standard inoculum: gas-phase storage. Appl Microbiol. 1968 Jun;16(6):912–916. doi: 10.1128/am.16.6.912-916.1968. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. OROSHNIK W., MEBANE A. D. THE POLYENE ANTIFUNGAL ANTIBIOTICS. Fortschr Chem Org Naturst. 1963;21:17–79. doi: 10.1007/978-3-7091-7149-3_2. [DOI] [PubMed] [Google Scholar]
  17. Pandey R. C., Rinehart K. L., Jr Polyene antibiotics. V. Characterization of components of the filipin complex by mass spectrometry. J Antibiot (Tokyo) 1970 Aug;23(8):414–417. doi: 10.7164/antibiotics.23.414. [DOI] [PubMed] [Google Scholar]
  18. Reiblein W. J., Watkins P. D., Wagman G. H. Binding of gentamicin and other aminoglycoside antibiotics to mycelium of various actinomycetes. Antimicrob Agents Chemother. 1973 Dec;4(6):602–606. doi: 10.1128/aac.4.6.602. [DOI] [PMC free article] [PubMed] [Google Scholar]
  19. Schaffner C. P., Gordon H. W. The hypocholesterolemic activity of orally administered polyene macrolides. Proc Natl Acad Sci U S A. 1968 Sep;61(1):36–41. doi: 10.1073/pnas.61.1.36. [DOI] [PMC free article] [PubMed] [Google Scholar]
  20. Sessa G., Weissmann G. Effects of four components of the polyene antibiotic, filipin, on phospholipid spherules (liposomes) and erythrocytes. J Biol Chem. 1968 Aug 25;243(16):4364–4371. [PubMed] [Google Scholar]
  21. Weissmann G., Sessa G. The action of polyene antibiotics on phospholipid-cholesterol structures. J Biol Chem. 1967 Feb 25;242(4):616–625. [PubMed] [Google Scholar]
  22. van Zutphen H., Demel R. A., Norman A. W., van Deenen L. L. The action of polyene antibiotics on lipid bilayer membranes in the presence of several cations and anions. Biochim Biophys Acta. 1971 Aug 13;241(2):310–330. doi: 10.1016/0005-2736(71)90031-9. [DOI] [PubMed] [Google Scholar]

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

RESOURCES