Advertisement

Doklady Chemistry

, Volume 487, Issue 1, pp 173–176 | Cite as

Peptide Derivatives of Some Physiologically Active Substances

  • V. P. ShevchenkoEmail author
  • L. A. Andreeva
  • I. Yu. Nagaev
  • N. F. Myasoedov
CHEMISTRY
  • 5 Downloads

Abstract

The synthesis of Boc-Gly-Pro-Dox, Boc-Gly-Pro-DOPA, and Boc-Gly-Pro-Srt and their deuterated analogues was carried out. The condensation is accompanied by side reactions, which could be minimized by optimizing the reaction conditions. The most versatile approach to the synthesis of Boc-Gly-Pro-Dox, Boc-Gly-Pro-DOPA, and Boc-Gly-Pro-Srt and their deuterated analogues is condensation of Boc-Gly-Pro or Boc-Gly-[2H]Pro with the amino groups of dopamine, serotonin, and doxorubicin. For the introduction of hydrogen isotopes into ΔPro, hydrogenation of its aqueous solution followed by condensation of the reduced proline with Boc-GlyOSu is recommended. Mass spectrometry was used to determine the content of isotopomers in the deuterated products.

Notes

FUNDING

This work was partially supported by the Basic Research Program of the Presidium of the RAS “Basic Research for Biomedical Technologies.”

REFERENCES

  1. 1.
    Semenova, A.I., Prakt. Onkol., 2009, vol. 10, no. 3, pp. 168–176.Google Scholar
  2. 2.
    Minotti, G., Menna, P., Salvatorelli, E., Cairo, G., and Gianni, L., Pharmacol. Rev., 2004, vol. 56, no. 2, pp. 185–229.CrossRefGoogle Scholar
  3. 3.
    Octavia, Y., Tocchetti, C.G., Gabrielson, K.L., Janssens, S., Crijns, H.J., and Moens, A.L., J. Mol. Cell. Cardiol., 2012, vol. 52, no. 6, pp. 1213–1225.CrossRefGoogle Scholar
  4. 4.
    Huang, S., Fang, R., Xu, J., Qiu, S., Zhang, H., Du, J., and Cai, S., J. Drug Target., 2011, vol. 19, no. 7, pp. 487–496.Google Scholar
  5. 5.
    Greenstein, J.P. and Winitz, M., Chemistry of Amino Acids, Wiley, 1961. Translated under the title Khimiya aminokislot i peptidov, Moscow: Mir, 1965.Google Scholar
  6. 6.
    Gershkovich, A.A. and Kibirev, V.K., Khimicheskii sintez peptidov (Chemical Synthesis of Peptides), Kiev: Naukova Dumka, 1992.Google Scholar
  7. 7.
    Radchenko, E.V., Karpov, P.V., Sosnin, S.B., Dyabina, A.S., Sosnina, E.A., Palyulin, V.A., and Zefirov, N.S., Abstracts of Papers, XX Mendeleev Congress on General and Applied Chemistry, Yekaterinburg, September 26–30, 2016, p. 432.Google Scholar
  8. 8.
    Dyabina, A.S., Radchenko, E.V., Palyulin, V.A., and Zefirov, N.S., Dokl. Biochem. Biophys., 2016, vol. 470, pp. 372–374.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • V. P. Shevchenko
    • 1
    Email author
  • L. A. Andreeva
    • 1
  • I. Yu. Nagaev
    • 1
  • N. F. Myasoedov
    • 1
  1. 1.Institute of Molecular Genetics, Russian Academy of SciencesMoscowRussia

Personalised recommendations