Skip to main content

Advertisement

SpringerLink
Log in

Modeling of the mechanism of hydrolysis of succinylcholine in the active site of native and modified (Asp70Gly) human butyrylcholinesterase

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The quantum mechanics/molecular mechanics method was used to model the mechanism of hydrolysis of succinylcholine in the active site of native butyrylcholinesterase and the Asp70Gly single mutant enzyme. The energy diagram for the reaction pathway of the acylation was constructed, and the effect of the mutation on the reaction mechanism and energy characteristics of the process are discussed.

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. M. Barbosa, O. Rios, M. Velásquez, J. Villalobos, J. Ehrmanns, Surg. Neurol., 2001, 55, 106.

    Article  CAS  Google Scholar 

  2. C.-G. Zhan, F. Zheng, D. W. Landry, J. Am. Chem. Soc., 2003, 125, 2462.

    Article  CAS  Google Scholar 

  3. L. G. Sokolovskaya, L. V. Sigolaeva, A. V. Eremenko, I. N. Kurochkin, G. F. Makhaeva, V. V. Malygin, I. E. Zykova, V. I. Kholstov, N. V. Zav’yalova, S. D. Varfolomeev, Khim. Biol. Bezopasnost’ [Chem. Biol. Safety], 2004, 13–14, 21 (in Russian).

    Google Scholar 

  4. M. Pirmohamed, B. K. Park, Trends Pharmacol. Sci., 2001, 22, 298.

    Article  CAS  Google Scholar 

  5. M. C. Mcguire, C. P. Nogueira, C. F. Bartels, H. Light-stone, A. Hajra, A. F. Van der Spek, O. Lockridge, B. N. La Du, Proc. Natl. Acad. Sci. USA, 1989, 86, 953.

    Article  CAS  Google Scholar 

  6. D. Suarez, N. Diaz, J. Fontecilla-Camps, M. J. Field, Bio-chemistry, 2006, 45, 7529.

    CAS  Google Scholar 

  7. C.-G. Zhan, D. Gao, Biophys. J., 2005, 89, 3863.

    Article  CAS  Google Scholar 

  8. P. Masson, P. Legrand, C. F. Bartels, M.-T. Froment, L. M. Schopfer, O. Lockridge, Biochemistry, 1997, 36, 2266.

    Article  CAS  Google Scholar 

  9. S. D. Varfolomeev, Khimicheskaya enzimologiya [Chemical Enzymology], Akademiya, Moscow, 2005, 480 pp. (in Russian).

    Google Scholar 

  10. K. B. Bravaya, A. V. Bochenkova, B. L. Grigorenko, I. A. Topol, S. Burt, A. V. Nemukhin, J. Chem. Theory Comput., 2006, 2, 1168.

    Article  CAS  Google Scholar 

  11. B. L. Grigorenko, A. V. Nemukhin, M. S. Shadrina, I. A. Topol, S. K. Burt, Proteins: Structure, Function, Bioinformatics, 2007, 66, 456.

    Article  CAS  Google Scholar 

  12. B. L. Grigorenko, A. V. Rogov, I. A. Topol, S. K. Burt, H. M. Martinez, A. V. Nemukhin, Proc. Natl. Acad. Sci., 2007, 104, 7057.

    Article  CAS  Google Scholar 

  13. A. V. Nemukhin, S. V. Lushchekina, A. V. Bochenkova, A. A. Golubeva, S. D. Varfolomeev, J. Mol. Model., 2008, 14, 409.

    Google Scholar 

  14. Y. Zhang, J. Kua, J. A. McCammon, J. Am. Chem. Soc., 2002, 124, 10572.

    Article  CAS  Google Scholar 

  15. H. M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T. N. Bhat, H. Weissig, I. N. Shindyalov, P. E. Bourne, Nucleic Acids Res., 2000, 28, 235.

    Article  CAS  Google Scholar 

  16. J. M. Word, S. C. Lovell, T. H. Labean, H. C. Taylor, M. E. Zalis, B.K. Presley, J. S. Richardson, D. C. Richardson, J. Mol. Biol., 1999, 285, 1711.

    Article  CAS  Google Scholar 

  17. D. M. Quinn, Chem. Rev., 1987, 87, 955.

    Article  CAS  Google Scholar 

  18. M. A. Massiah, C. Viragh, P. M. Reddy, I. M. Kovach, J. Johnson, T. L. Rosenberry, A. S. Mildvan, Biochemistry, 2001, 40, 5682.

    Article  CAS  Google Scholar 

  19. G. M. Morris, D. S. Goodsell, R. S. Halliday, R. Huey, W. E. Hart, R. K. Belew, A. J. Olson, J. Am. Chem. Soc., 1998, 19, 1639.

    CAS  Google Scholar 

  20. J. W. Ponder, TINKER: Software Tools for Molecular Design, Version 3.7, 1999, Washington University: St. Louis.

    Google Scholar 

  21. T. A. Halgren, J. Comput. Chem., 1996, 17, 490.

    Article  CAS  Google Scholar 

  22. B. L. Grigorenko, A. V. Nemukhin, I. A. Topol, S. K. Burt, J. Phys. Chem. A, 2002, 106, 10663.

    Article  CAS  Google Scholar 

  23. A. V. Nemukhin, B. L. Grigorenko, I. A. Topol, S. K. Burt, J. Comput. Chem., 2003, 24, 1410.

    Article  CAS  Google Scholar 

  24. J. Wang, R. M. Wolf, J. W. Caldwell, P. A. Kollman, D. A. Case, J. Comput. Chem., 2004, 25, 1157.

    Article  CAS  Google Scholar 

  25. A. A. Granovsky, PC GAMESS/Firefly version 7.1.F, http://classic.chem.msu.su/gran/gamess/index.html.

  26. P. Masson, M.-T. Froment, P. L. Fortier, J. E. Visicchio, C. F. Bartels, O. Lockridge, Biochim. Biophys. Acta Prot. Struct. Mol. Enzym., 1998, 1387, 41.

    Article  CAS  Google Scholar 

  27. M. Fuxreiter, A. Warshel, J. Am. Chem. Soc., 1998, 120, 183.

    Article  CAS  Google Scholar 

  28. A. V. Nemukhin, B. L. Grigorenko, A. V. Rogov, I. A. Topol, S. K. Burt, Theor. Chem. Acc., 2004, 111, 36.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 119334, Moscow, Russian Federation

    S. V. Lushchekina, A. V. Nemukhin & S. D. Varfolomeev

  2. Department of Chemistry, M. V. Lomonosov Moscow State University, 1 Leninskie Gory, 119992, Moscow, Russian Federation

    B. L. Grigorenko, D. I. Morozov, I. V. Polyakov, A. V. Nemukhin & S. D. Varfolomeev

Authors
  1. S. V. Lushchekina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. B. L. Grigorenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. D. I. Morozov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. V. Polyakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. V. Nemukhin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. S. D. Varfolomeev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. V. Lushchekina.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 56–61, January, 2010.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lushchekina, S.V., Grigorenko, B.L., Morozov, D.I. et al. Modeling of the mechanism of hydrolysis of succinylcholine in the active site of native and modified (Asp70Gly) human butyrylcholinesterase. Russ Chem Bull 59, 55–60 (2010). https://doi.org/10.1007/s11172-010-0044-0

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-010-0044-0

Search

Navigation