Advertisement

Doklady Physical Chemistry

, Volume 484, Issue 1, pp 15–19 | Cite as

Solid-State Catalytic Isotope Exchange of Hydrogen for Deuterium in Cyclopropylglycine

  • A. K. DadayanEmail author
  • Yu. A. Borisov
  • E. V. Bocharov
  • Yu. A. Zolotarev
  • I. Yu. Nagaev
  • N. F. Myasoedov
PHYSICAL CHEMISTRY
  • 30 Downloads

Abstract

The reaction of spillover hydrogen (SH) with cyclopropylglycine (cPG) in high-temperature solid-state catalytic hydrogen isotope exchange (HTCIE) has been studied experimentally and using density functional theory (DFT). NMR spectroscopy and mass spectrometry have shown a high regioselectivity and stereoselectivity for the reaction of spillover hydrogen with cPG fragments. The Gly fragment has been shown to be the most reactive in HTCIE, for which high stereoselectivity of substitution of hydrogen by deuterium has been demonstrated.

Notes

ACKNOWLEDGMENTS

This work was supported by the Presidium of the RAS (Program “Molecular and Cell Biology and Postgenomic Technologies”).

REFERENCES

  1. 1.
    Boudart, M., Vannice, M.A., and Benson, J.E., J. Phys. Chem., 1969, vol. 64, pp. 171–177.Google Scholar
  2. 2.
    Conner, W.C. and Falconer, J.L., Chem. Rev., 1995, vol. 95, pp. 759–788.CrossRefGoogle Scholar
  3. 3.
    Yang, M., Nakamura, I., and Fujuimoto, K., J. Appl. Catal., Gen., 1996, vol. 144, pp. 221–235.Google Scholar
  4. 4.
    Stumbo, A.M., Grande, P., and Delmon, B., Stud. Surf. Sci. Catal., 1997, vol. 112, pp. 211–220.CrossRefGoogle Scholar
  5. 5.
    Roessner, F., Roland, U., and Braunschweig, T., J. Chem. Soc., Faraday Trans., 1995, vol. 91, pp. 1536–1545.CrossRefGoogle Scholar
  6. 6.
    Zolotarev, Yu.A., Dadayan, A.K., Borisov, Yu.A., and Kozik, V.S., Chem. Rev., 2010, vol. 110, pp. 5425–5446.CrossRefGoogle Scholar
  7. 7.
    Zolotarev, Yu.A., Dorokhova, E.M., Nezavibatko, V.N., Borisov, Yu.A., Rosenberg, S.G., and Myasoedov, N.F., Amino Acids, 1995, vol. 8, pp. 353–365.Google Scholar
  8. 8.
    Zolotarev, Yu.A., Dadayan, A.K., Borisov, Yu.A., Kozik, V.S., Nazimov, I.V., Ziganshin, R.H., Bocharov, E.V., Chizhov, A.O., and Myasoedov, N.F., J. Phys. Chem. C, 2013, vol. 117, no. 33, pp. 16878–16884.CrossRefGoogle Scholar
  9. 9.
    Gaussian 09W, Version 7.0, Copyright 1995-09 Gaussian, Inc.Google Scholar
  10. 10.
    Gonzalez, C. and Schlegel, H.B., J. Phys. Chem., 1990, vol. 94, no. 14, pp. 5523–5527.CrossRefGoogle Scholar
  11. 11.
    Schlegel, H.B. and Robb, M.A., Chem. Phys. Lett., 1982, vol. 93, no. 1, pp. 43–46.CrossRefGoogle Scholar
  12. 12.
    Schlegel, H.B., Geometry optimization on potential energy surfaces, in Modern Electronic Structure Theory, Yarkony, D.R., Ed., Singapore: World Scientific, 1995.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • A. K. Dadayan
    • 1
    Email author
  • Yu. A. Borisov
    • 2
  • E. V. Bocharov
    • 3
    • 4
    • 5
  • Yu. A. Zolotarev
    • 1
  • I. Yu. Nagaev
    • 1
  • N. F. Myasoedov
    • 1
  1. 1.Institute of Molecular Genetics, Russian Academy of SciencesMoscowRussia
  2. 2.Nesmeyanov Institute of Organoelement Compounds, Russian Academy of SciencesMoscowRussia
  3. 3.Russian Research Center “Kurchatov Institute”MoscowRussia
  4. 4.Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of SciencesMoscowRussia
  5. 5.Moscow Institute of Physics and Technology (State University)DolgoprudnyiRussia

Personalised recommendations