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Peptide derivatives of tylosin-related macrolides

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Abstract

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.

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Abbreviations

βAla:

β-alanine

DCC:

N,N′-dicyclohexylcarbodiimide

Des:

desmycosin

DIEA:

diisopropylethylamine

DMAP:

4-dimethylaminopyridine

DNPH:

2,4-dinitrophenylhydrazine

Glyc:

glycolyl

HBTU:

N-hydroxybenzotriazolyluronium hexafluorophosphate

MeOTr:

4-monomethoxytrityl

OMT:

O-mycaminosyltylonolide

PTC:

the peptidyl transferase center

Tyl:

tylosin. All amino acids of the L series

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Authors and Affiliations

  1. Belozersky Research Institute of Physicochemical Biology, Faculty of Chemistry, Moscow State University, Vorob’evy Gory, Moscow, 119992, Russia

    G. A. Korshunova, N. V. Sumbatyan, N. V. Fedorova, I. V. Kuznetsova, A. V. Shishkina & A. A. Bogdanov

Authors
  1. G. A. Korshunova
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  2. N. V. Sumbatyan
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  3. N. V. Fedorova
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  4. I. V. Kuznetsova
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  5. A. V. Shishkina
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  6. A. A. Bogdanov
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Corresponding author

Correspondence to G. A. Korshunova.

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Original Russian Text © G.A. Korshunova, N.V. Sumbatyan, N.V. Fedorova, I.V. Kuznetsova, A.V. Shishkina, A.A. Bogdanov, 2007, published in Bioorganicheskaya Khimiya, 2007, Vol. 33, No. 2, pp. 235–244.

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Korshunova, G.A., Sumbatyan, N.V., Fedorova, N.V. et al. Peptide derivatives of tylosin-related macrolides. Russ J Bioorg Chem 33, 218–226 (2007). https://doi.org/10.1134/S1068162007020033

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  • DOI: https://doi.org/10.1134/S1068162007020033

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