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Phosphorylation of Tyrosine and Tyr-Thr-Lys Tripeptide with Cyclohexylmethyl- and (Deuteromethyl)phosphonochloridates

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Abstract

Methods for phosphorylation of tyrosine and Tyr-Thr-Lys tripeptide with cyclohexylmethyl(deuteromethyl)phosphonochloridates have been developed. These products can be used as reference compounds in the analysis of blood plasma of patients presumably exposed to cyclohexylmethylphosphonofluoridate (cyclosarin) action. Conditions for the separation and purification of the synthesized intermediates by means of chromatography have been determined and optimized, allowing high-purity phosphorylated products at the final stage of the synthesis.

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REFERENCES

  1. Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and Their Destruction, Technical Secretariat of the Organization for the Prohibition of Chemical Weapons, The Hague, 1993. https://www.opcw.org/.

  2. Work Instruction for the Reporting of the Results of the Opcw Biomedical Proficiency Tests. Quality Management System Document no. QDOC/LAB/WI/BioPT04, Revision no. 3, 2019. https://www.opcw.org/.

  3. 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  PubMed  Google Scholar 

  4. 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  PubMed  Google Scholar 

  5. Sato, A., Yoshida, M., and Hara, S., Chem. Commun., 2008, vol. 14, no. 46, p. 6242. https://doi.org/10.1039/B814804J

    Article  Google Scholar 

  6. Nakamura, H., Fujiwara, M., and Yamamoto, Y., J. Org. Chem., 1998, vol. 63, no. 21, p. 7529. https://doi.org/10.1021/jo980818r

    Article  CAS  PubMed  Google Scholar 

  7. 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  PubMed  Google Scholar 

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

  9. 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 

  10. Balaev, A.N., Osipov, V.N., and Fedorov, V.E., Pharm. Chem. J., 2014, vol. 48, no. 5, p. 340. https://doi.org/10.1007/s11094-014-1106-7

    Article  CAS  Google Scholar 

  11. Balaev, A.N., Osipov, V.N., Okhmanovich, K.A., Ruchko, E.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 

  12. Balaev, A.N., Osipov, V.N., Okhmanovich, K.A., Ruchko, E.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 

  13. 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, no. 1, p. 246. https://doi.org/10.1021/jm050518j

    Article  CAS  PubMed  Google Scholar 

  14. Rodin, I.A., Baygildiev, T.M., Krylov, V.I., Osipov, V.N., Krylov, I.I., Yashkir, V.A, and Rybalchenko, I.V., Russ. J. Gen. Chem., 2019, vol. 89, no. 10, p. 2103. https://doi.org/10.1134/S1070363219100189

    Article  CAS  Google Scholar 

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Funding

This study was financially supported by the Russian Science Foundation (project no. 19-13-00057).

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Correspondence to I. A. Rodin.

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Rodin, I.A., Baygildiev, T.M., Krylov, V.I. et al. Phosphorylation of Tyrosine and Tyr-Thr-Lys Tripeptide with Cyclohexylmethyl- and (Deuteromethyl)phosphonochloridates. Russ J Gen Chem 90, 619–623 (2020). https://doi.org/10.1134/S1070363220040106

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  • DOI: https://doi.org/10.1134/S1070363220040106

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