Skip to main content
SpringerLink
Log in

Synthesis of the Tripeptides Tyr-Thr-Lys Phosphorylated with Isopropyl Methyl- and (Deuteromethyl)phosphonochloridates as Reference Standards for the Analysis of Biomedical Samples

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

A procedure for the phosphorylation of the tripeptide Tyr-Thr-Lys with isopropyl methyl- or (deuteromethyl)phosphonochloridate is developed. The phosphorylated tripeptides are intended for use as reference standards in the analysis of blood samples of people suspected to have been exposed to acetylcholinesterase inhibitors. Conditions of hromatographic separation and purification of the synthesized compounds are determined and optimized, which ensures the preparation of high-purity phosphorylated tripeptides.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction. https://www.opcw.org/chemical-weapons-convention.

  2. Black, R.M. and Read, R.W., Arch. Toxicol., 2013, vol. 87, no. 3, p. 421. https://doi.org/10.1007/s00204-012-1005-1

    Article  CAS  Google Scholar 

  3. Williams, N.H., Harrison, J.M., Read, R.W., and Black, R.M., Arch. Toxicol., 2007, vol. 81, no. 9, p. 627. https://doi.org/10.1007/s00204-007-0191-8

    Article  CAS  Google Scholar 

  4. Sato, A., Yoshida, M., and Hara, S., Chem. Commun., 2008, no. 46, p. 6242. https://doi.org/10.1039/B814804J

  5. Gershkovich, A.A. and Kibirev, V.K., Sintez peptidov. Reagenty i metody (Synthesis of Peptides. Reagents and Methods), Kiev: Naukova Dumka, 1987.

    Google Scholar 

  6. Balaev, A.N., Osipov, V.N., Okhmanovich, K.A., and Fedorov, V.E., Pharm. Chem. J., 2014, vol. 48, no. 3, p. 217. https://doi.org/10.1007/s11094-014-1080-0

    Article  CAS  Google Scholar 

  7. Balaev, A.N., Osipov, V.N., and Fedorov, V.E., Pharm. Chem. J., 2014, vol. 48, p. 340. https://doi.org/10.1007/s11094-014-1106-7

    Article  CAS  Google Scholar 

  8. Balaev, A.N., Osipov, V.N., Okhmanovich, K.A., Ruchko, Ye.A., Kolotaev, A.V., and Khachatryan, D.S., Russ. Chem. Bull., 2016, vol. 65, no. 11, p. 2766. https://doi.org/10.1007/s11172-016-1651-1

    Article  CAS  Google Scholar 

  9. Balaev, A.N., Osipov, V.N., Okhmanovich, K.A., Ruchko, Ye.A., Baryshnikova, M.A., and Khachatryan, D.S., Russ. Chem. Bull., 2016, vol. 65, no. 12, p. 2948. https://doi.org/10.1007/s11172-016-1683-6

    Article  CAS  Google Scholar 

  10. Bennet, A.J., Kovach, I.M, and Bibbs, J.A., J. Am. Chem. Soc., 1989, vol. 111, p. 6424 https://doi.org/10.1021/ja00198a067

    Article  CAS  Google Scholar 

  11. Briseno-Roa, L., Hill, J., Notman, S., Sellers, D., Smith, A.P., Timperley, C.M., Wetherell, J., Williams, N.H., Williams, G.R., Fersht, A.R., and Griffiths, A.D., J. Med. Chem., 2006, vol. 49, p. 246. https://doi.org/10.1021/jm050518j

    Article  CAS  Google Scholar 

Download references

Funding

This work was supported by the Russian Science Foundation (grant no. 19-13-00057) for Lomonosov Moscow State University.

Author information

Authors and Affiliations

  1. Chemical Department, Lomonosov Moscow State University, Moscow, 119991, Russia

    I. A. Rodin & T. M. Baygildiev

  2. Farmsintez ZAO, Moscow, 111024, Russia

    V. N. Osipov

  3. 27 Research Center, Ministry of Defense of the Russian Federation, Moscow, 105005, Russia

    V. I. Krylov, I. I. Krylov, V. A. Yashkir & I. V. Rybalchenko

Authors
  1. I. A. Rodin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. M. Baygildiev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. I. Krylov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. N. Osipov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. I. I. Krylov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. V. A. Yashkir
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. I. V. Rybalchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. A. Rodin.

Ethics declarations

No conflict of interest was declared by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rodin, I.A., Baygildiev, T.M., Krylov, V.I. et al. Synthesis of the Tripeptides Tyr-Thr-Lys Phosphorylated with Isopropyl Methyl- and (Deuteromethyl)phosphonochloridates as Reference Standards for the Analysis of Biomedical Samples. Russ J Gen Chem 89, 2103–2107 (2019). https://doi.org/10.1134/S1070363219100189

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363219100189

Keywords

Search

Navigation