A new biologically active component, antibiotic eremomycin B, was isolated from the culture liquid of Amycolatopsis orientalis subsp. eremomycini, the producing strain for antibiotic eremomycin. Its structure was established by NMR spectroscopy and mass spectrometry. Eremomycin B was shown to differ from eremomycin by the presence of an N-carboxymethyl substituent in the disaccharide eremosamine fragment.

NMR, structure, antibiotics, eremomycin, eremomycin B, eremosamine

Publication DOI: 10.1134/S1068162009040128
Journal NLM ID: 9420101
Publisher: Springer Science and Business Media
Correspondence: shashioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Gauze Research Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, MALDI-TOF MS, paper chromatography, electrophoresis, UV, ROESY, CC, precipitation, HMBC
 

• Compound ID: 13326
  

  a-Erep3N3CMe-(1-8)-+ | a-Erep3N3CMe-(1-2)-b-D-Glcp-(1-4)-Subst Subst = SMILES CN[C@H](CC(C)C)C(=O)N[C@H]7C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H]5C(=O)N[C@@H]2C(=O)N[C@@H](C(=O)N[C@H](C(=O)O)c1cc(O)cc(O)c1c3cc2ccc3O){8}[C@H](O)c4ccc(cc4)Oc8cc5cc(Oc6ccc(cc6Cl)[C@H]7O){4}c8O

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  Structure type: oligomer ; 1558 [M+H]+, 1580 [M+Na]+, 1596 [M+K]+
  Trivial name: eremomycin
  Compound class: glycoside
  
   
  
  Amycolatopsis orientalis ssp. eremomycini
  CSDB ID 44053 (all data & tools)
• Compound ID: 13327
  

  a-Erep3N3CMe-(1-8)-+ | Gly-(2-3)-a-Erep3N3CMe-(1-2)-b-D-Glcp-(1-4)-Subst Subst = SMILES CN[C@H](CC(C)C)C(=O)N[C@H]7C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H]5C(=O)N[C@@H]2C(=O)N[C@@H](C(=O)N[C@H](C(=O)O)c1cc(O)cc(O)c1c3cc2ccc3O){8}[C@H](O)c4ccc(cc4)Oc8cc5cc(Oc6ccc(cc6Cl)[C@H]7O){4}c8O

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  Structure type: oligomer ; 1617 [M+H]+, 1639 [M+Na]+, 1655 [M+K]+
  Trivial name: eremomycin B
  Compound class: glycoside
  
   
  
  Amycolatopsis orientalis ssp. eremomycini
  CSDB ID 44054 (all data & tools)