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Russian Journal of Organic Chemistry

, Volume 55, Issue 6, pp 762–770 | Cite as

Synthesis of New Purine Derivatives Containing α- and ω-Amino Acid Fragments

  • V. V. Musiyak
  • I. A. Nizova
  • T. V. Matveeva
  • G. L. Levit
  • V. P. KrasnovEmail author
  • V. N. Charushin
Article
  • 11 Downloads

Abstract

New conjugates of purine and 2-aminopurine with several α- and ω-amino acids have been synthesized following two approaches based on the condensation and nucleophilic substitution reactions. The enantiomeric purity of the isolated compounds has been confirmed by reversed-phase HPLC using a chiral stationary phase to demonstrate the absence of racemization during the synthesis. The conjugates are inactive against Mycobacterium tuberculosis H37Rv.

Keywords

purine derivatives amino acids enantiomers peptide synthesis nucleophilic substitution 

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Notes

Acknowledgments

The authors thank Dr. M.I. Kodess and M.A. Ezhikova for recording the NMR spectra, Dr. I.N. Ganebnykh for recording the high-resolution mass spectra, the Group of Elemental Analysis under the guidance of Dr. L.N. Bazhenova (Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences), Dr. A.A. Tumashov for performing HPLC analyses, and Dr. M.A. Kravchenko for performing in vitro biological studies. This study was carried out using the equipment of the “Spectroscopy and Analysis of Organic Compounds” joint center.

Funding

This study was performed under financial support by the Russian Science Foundation (project no. 19-13-00231).

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Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • V. V. Musiyak
    • 1
  • I. A. Nizova
    • 1
  • T. V. Matveeva
    • 1
  • G. L. Levit
    • 1
  • V. P. Krasnov
    • 1
    Email author
  • V. N. Charushin
    • 1
  1. 1.Postovskii Institute of Organic Synthesis, Ural BranchRussian Academy of SciencesYekaterinburgRussia

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