Russian Journal of Bioorganic Chemistry

, Volume 33, Issue 2, pp 218–226 | Cite as

Peptide derivatives of tylosin-related macrolides

  • G. A. KorshunovaEmail author
  • N. V. Sumbatyan
  • N. V. Fedorova
  • I. V. Kuznetsova
  • A. V. Shishkina
  • A. A. Bogdanov


Approaches to the synthesis of model compounds based on the tylosin-related macrolides desmycosin and O=mycaminosyltylonolide were developed to study the conformation and topography of the nascent peptide chain in the ribosome tunnel using specially designed peptide derivatives of macrolide antibiotics. A method for selective bromoacetylation of desmycosin at the hydroxyl group of mycinose was developed, which involves preliminary acetylation of mycaminose. The reaction of the 4″-bromoacetyl derivative of the antibiotic with cesium salts of the dipeptide Boc-Ala-Ala-OH and the hexapeptide MeOTr-Gly-Pro-Gly-Pro-Gly-Pro-OH led to the corresponding peptide derivatives of desmycosin. The protected peptides Boc-Ala-Ala-OH, Boc-Ala-Ala-Phe-OH, and Boc-Gly-Pro-Gly-Pro-Gly-Pro-OH were condensed with the C23-hydroxyl group of O-mycaminosyltylonolide.

Key words

tylosin desmycosin O-mycaminosyltylonolide peptide derivatives of macrolides 

















N-hydroxybenzotriazolyluronium hexafluorophosphate






the peptidyl transferase center


tylosin. All amino acids of the L series


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Copyright information

© Pleiades Publishing, Inc. 2007

Authors and Affiliations

  • G. A. Korshunova
    • 1
    Email author
  • N. V. Sumbatyan
    • 1
  • N. V. Fedorova
    • 1
  • I. V. Kuznetsova
    • 1
  • A. V. Shishkina
    • 1
  • A. A. Bogdanov
    • 1
  1. 1.Belozersky Research Institute of Physicochemical Biology, Faculty of ChemistryMoscow State UniversityVorob’evy Gory, MoscowRussia

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