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Chemical Compound Review: 

Erythronolide B     14-ethyl-4,6,7,12- tetrahydroxy-3,5,7,9,11...

 
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Disease relevance of Erythronolide B

 

High impact information on Erythronolide B

  • This product resulted from targeted disruption of the gene, designated eryF (systematic nomenclature, CYP107), that apparently codes for the cytochrome P450, 6-deoxyerythronolide B (DEB) hydroxylase, which converts DEB to erythronolide B (EB) [2].
  • Collision induced dissociation sequential mass spectrometry was used to investigate the fragmentation of the heptaketide macrolide aglycones, 6-deoxyerythronolide B (6-dEB), erythronolide B (EB), and acetate-starter EB (Ac-EB) [3].
  • Genes that govern the formation of deoxysugars or their attachment to erythronolide B and 3 alpha-mycarosyl erythronolide B, intermediates of the biosynthesis of the 14-membered macrolide antibiotic erythromycin, were cloned from Saccharopolyspora erythraea (formerly Streptomyces erythreus) [4].
  • Chromosomal mutants carrying a deletion either in ORF7 or in one of the previously sequenced ORFs 13 and 14 have been constructed and shown to accumulate erythronolide B, as expected for eryB mutants [5].
  • Also, a chromosomal mutant was constructed for the previously sequenced ORF19 and shown to accumulate erythronolide B, as expected for an eryB mutant and consistent with its proposed role as an epimerase in dTDP-mycarose biosynthesis [6].
 

Chemical compound and disease context of Erythronolide B

  • Transformation of erythronolide B to new antibiotics was attempted by feeding this compound during the fermentation of Streptomyces antibioticus ATCC31771, a blocked mutant of an oleandomycin producing strain [7].
 

Gene context of Erythronolide B

  • Similarly, chromosomal mutants carrying a deletion in either ORF8, ORF9, or one of the previously sequenced ORFs 17 and 18 have been constructed and shown to accumulate 3-alpha-mycarosyl erythronolide B, as expected for eryC mutants [5].

References

  1. A defined system for hybrid macrolide biosynthesis in Saccharopolyspora erythraea. Gaisser, S., Reather, J., Wirtz, G., Kellenberger, L., Staunton, J., Leadlay, P.F. Mol. Microbiol. (2000)
  2. An erythromycin derivative produced by targeted gene disruption in Saccharopolyspora erythraea. Weber, J.M., Leung, J.O., Swanson, S.J., Idler, K.B., McAlpine, J.B. Science (1991)
  3. Structural elucidation studies on 14- and 16-membered macrolide aglycones by accurate-mass electrospray sequential mass spectrometry. Roddis, M., Gates, P., Roddis, Y., Staunton, J. J. Am. Soc. Mass Spectrom. (2002)
  4. Cloning of genes governing the deoxysugar portion of the erythromycin biosynthesis pathway in Saccharopolyspora erythraea (Streptomyces erythreus). Vara, J., Lewandowska-Skarbek, M., Wang, Y.G., Donadio, S., Hutchinson, C.R. J. Bacteriol. (1989)
  5. Targeted gene inactivation for the elucidation of deoxysugar biosynthesis in the erythromycin producer Saccharopolyspora erythraea. Salah-Bey, K., Doumith, M., Michel, J.M., Haydock, S., Cortés, J., Leadlay, P.F., Raynal, M.C. Mol. Gen. Genet. (1998)
  6. Analysis of eryBI, eryBIII and eryBVII from the erythromycin biosynthetic gene cluster in Saccharopolyspora erythraea. Gaisser, S., Böhm, G.A., Doumith, M., Raynal, M.C., Dhillon, N., Cortés, J., Leadlay, P.F. Mol. Gen. Genet. (1998)
  7. Biological conversion of erythronolide B, an intermediate of erythromycin biogenesis, into new "hybrid" macrolide antibiotics. Spagnoli, R., Cappelletti, L., Toscano, L. J. Antibiot. (1983)
 
 
 
 
 
 
 
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