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

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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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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  • DOI: https://doi.org/10.1134/S1068162010020159

Key words

  • macrolides
  • chemical modification
  • reductive amination
  • oximes
  • peptide derivatives
  • tylosin
  • desmycosin
  • 5-O-mycaminosyltylonolide