Skip to main content
SpringerLink
Log in

Synthesis of new tetrazolyl derivatives of L- and D-phenylalanine

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

Abstract

New tetrazolyl derivatives of L- and D-phenylalanine were synthesized by azidation of n-propyl esters of (2S)- and (2R)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-aminophenyl)propionic acids and by a series of subsequent chemical transformations. The structure and individuality of the compounds obtained were confirmed by using a complex of spectral and chromatographic methods.

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. Ostrovskii, V.A., Koldobskii, G.I., and Trifonov, R.E., Compr. Heterocycl. Chem. III, Katritzky, A.R., Ramsden, C.A., Scriven, E.F.V., Taylor, R.J.K., and Zhdankin, V.V., Eds., Oxford: Elsevier, 2008, vol. 6, p. 257.

    Article  Google Scholar 

  2. Ostrovskii V.A., Trifonov R.E., Popova E.A., Russ. Chem. Bull., 2012, vol. 61, p. 768.

    Article  CAS  Google Scholar 

  3. Popova, E.A. and Trifonov, R.E., Russ. Chem. Rev., 2015, vol. 84, p. 891.

    Article  CAS  Google Scholar 

  4. Voitekhovich, S.V., Gaponik, P.N., Grigor’ev, Yu.V., and Ivashkevich, O.A., Khimicheskie problemy sozdaniya novykh materialov i tekhnologii (Chemical Problems of the Creation of New Materials and Technologies), 2008.

    Google Scholar 

  5. Herr, R.J., Bioorg. Med. Chem., 2002, vol. 10, p. 3379.

    Article  CAS  Google Scholar 

  6. Allen, F.H., Groom, C.R., Liebeschuetz, J.W., Bardwell, D.A., Olsson, T.S.G., and Wood, P.A., J. Chem. Inf. Model., 2012, vol. 52, p. 857.

    Article  CAS  Google Scholar 

  7. Popova, E.A., Nikolskaia, S.K., Gluzdikov, I.A., and Trifonov, R.E., Tetrahedron Lett., 2014, vol. 55, p. 5041.

    Article  CAS  Google Scholar 

  8. Jakubke, H.-D. and Jeschkeit, H., Aminosäuren, Peptide, Proteine, Weinheim, Verlag Chemie, 1982.

    Google Scholar 

  9. McMurray, J.S., Khabashesku, A., Birtwistle, J.S., and Wang, W., Tetrahedron Lett., 2000, vol. 41, p. 6555.

    Article  CAS  Google Scholar 

  10. Devies, J.S., and Mohammed, A.K.A., J. Chem. Soc., Perkin Trans. 2, 1984, p. 1723.

    Google Scholar 

  11. Qiu, J., Xu, B., and Huang, Z., Bioorg. Med. Chem., 2011, vol. 19, p. 5352.

    Article  CAS  Google Scholar 

  12. Gaponik, P.N., Khimicheskie problemy sozdaniya novykh materialov i tekhnologii (Chemical Problems of the Creation of New Materials and Technologies), 1998.

    Google Scholar 

  13. Gaponik, P.N., Karavai, V.P., Davshko, I.E., Degtyarik, M.M., and Bogatikov, A.N., Chem. Heterocycl. Compd., 1990, vol. 26, p. 1274.

    Article  Google Scholar 

  14. Chuprun, S.S., Popova, E.A., Mukhametshina, A.V., and Trifonov, R.E., Russ. J. Org. Chem., 2015, vol. 51, p. 1671.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State Technological Institute (Technical University), St. Petersburg, Russia

    V. V. Tolstyakov, E. S. Tolstobrova, O. S. Zarubina & R. E. Trifonov

  2. St. Petersburg State University, Universitetskaya nab. 7/9, St. Petersburg, 199034, Russia

    E. A. Popova, A. V. Protas, S. S. Chuprun & R. E. Trifonov

Authors
  1. V. V. Tolstyakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. S. Tolstobrova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. S. Zarubina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. A. Popova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. V. Protas
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. S. S. Chuprun
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. R. E. Trifonov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to R. E. Trifonov.

Additional information

Original Russian Text © V.V. Tolstyakov, E.S. Tolstobrova, O.S. Zarubina, E.A. Popova, A.V. Protas, S.S. Chuprun, R.Е. Trifonov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 11, pp. 1686–1690.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tolstyakov, V.V., Tolstobrova, E.S., Zarubina, O.S. et al. Synthesis of new tetrazolyl derivatives of L- and D-phenylalanine. Russ J Org Chem 52, 1681–1685 (2016). https://doi.org/10.1134/S1070428016110221

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428016110221

Search

Navigation