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Amino acid and peptide derivatives of the tylosin family of macrolide antibiotics modified by aldehyde function

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Abstract

Fourteen new functionally active amino acid and peptide derivatives of the antibiotics tylosin, desmycosin, and 5-O-mycaminosyltylonolide were synthesized in order to study the interaction of the growing polypeptide chain with the ribosomal tunnel. The conjugation of various amino acids and peptides with a macrolide aldehyde group was carried out by two methods: direct reductive amination with the isolation of the intermediate Schiff bases or through binding via oxime using the preliminarily obtained derivatives of 2-aminooxy-acetic acid.

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Abbreviations

Aoac:

2-aminooxyacetyl

Des:

desmycosin

DIEA:

N,N-diisopropylethylamine

HBTU:

O-(benzotriazolyl)-1,1,3,3-tetramethyluronium hexafluorophosphate

HOBt:

1-hydroxybenzotriazol

OMT:

5-O-mycaminosyltylonolide

PTC:

peptidyltransferase center

RT:

ribosomal tunnel

Tyl:

tylosi

Ual:

3-(uracilyl-1-yl)alanine

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Moscow, 119991, Russia

    N. V. Sumbatyan, I. V. Kuznetsova, V. V. Karpenko, V. A. Chertkov & A. A. Bogdanov

  2. Belozersky Institute of Physicochemical Biology, Moscow, 119991, Russia

    N. V. Fedorova, G. A. Korshunova & A. A. Bogdanov

Authors
  1. N. V. Sumbatyan
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  2. I. V. Kuznetsova
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  3. V. V. Karpenko
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  4. N. V. Fedorova
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  5. V. A. Chertkov
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  6. G. A. Korshunova
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  7. A. A. Bogdanov
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Correspondence to N. V. Sumbatyan.

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Original Russian Text © N.V. Sumbatyan, I.V. Kuznetsova, V.V. Karpenko, N.V. Fedorova, V.A. Chertkov, G.A. Korshunova, A.A. Bogdanov, 2010, published in Bioorganicheskaya Khimiya, 2010, Vol. 36, No. 2, pp. 265–276.

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Sumbatyan, N.V., Kuznetsova, I.V., Karpenko, V.V. et al. Amino acid and peptide derivatives of the tylosin family of macrolide antibiotics modified by aldehyde function. Russ J Bioorg Chem 36, 245–256 (2010). https://doi.org/10.1134/S1068162010020159

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