Skip to main content
SpringerLink
Log in

Chemo- and regioselective modification of l-histidine with tertiary cyanopropargylic alcohols

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

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Abstract

l-Histidine chemo- and regioselectively reacts with tertiary cyanopropargylic alcohols (4,4-di-alkyl-4-hydroxybut-2-ynenitriles) under mild conditions (water, 6.4 wt.% NaOH, 5—15 °C, 72—175 h) with the formation of new “unnatural” amino acids containing an iminodihydrofuran substituent in the amino group (50—70% yields).

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. L. Cao, G. Bandelac, A. Volgina, J. Korostoff, J. M. Di-Rienzo, Infect. Immun., 2008, 76, 2812.

    Article  CAS  Google Scholar 

  2. T. A. Romanova, P. O. Krasnov, A. A. Kuzubov, P. V. Avramov, Russ. J. Bioorg. Chem. (Engl. Transl.), 2004, 30, 124 [Bioorg. Khim., 2004, 30, 141].

    Article  CAS  Google Scholar 

  3. E. Deplazes, W. van Bronswijk, F. Zhu, L. D. Barron, S. Ma, L. A. Nafie, K. J. Jalkanen, Theor. Chem. Acc., 2008, 119, 155.

    Article  CAS  Google Scholar 

  4. A. D. Conigrave, S. J. Quinn, E. M. Brown, Proc. Natl. Acad. Sci. USA, 2000, 97, 4814.

    Article  CAS  Google Scholar 

  5. A. Kleemann, J. Engel, B. Kutscher, D. Reichert, Pharmaceutical Substances: Syntheses, Patents, Applications, Thieme, Stuttgart—New York, 2001, p. 1015.

    Google Scholar 

  6. G. A. Gusev, Z. Gaobin, K. Kobayashi, K. Jianhua, E. V. Moiseenko, N. G. Polukhina, T. Saitoe, E. Tao, V. A. Tsarev, Y. Huang, Bull. Lebedev Phys. Inst., 2008, 35, 247 [Kratk. Soobshch. Fiz. FIAN, 2008, 35, No. 8, 41].

    Article  Google Scholar 

  7. M. Remko, D. Fitz, B. M. Rode, Amino Acids, 2010, 39, 1309.

    Article  CAS  Google Scholar 

  8. M. E. Pickup, J. S. Dixon, J. R. Lowe, V. Wright, J. Rheumatol., 1980, 7, 71.

    CAS  Google Scholar 

  9. M. D. Mashkovskii, Lekarstvennye sredstva [Medicines], Novaya Volna, Moscow, 2003, v. 2, p. 124 (in Russian).

    Google Scholar 

  10. U. Rauen, S. Klempt, H. de Groot, Cell. Mol. Life Sci., 2007, 64, 192.

    Article  CAS  Google Scholar 

  11. L. A. Bokeriya, A. A. Boldyrev, R. R. Movsesyan, S. A. Alikhanov, E. S. Arzumanyan, E. D. Nisnevich, T. V. Artyukhina, R. A. Serov, Bull. Exp. Biol. Med., 2008, 145, 323.

    Article  CAS  Google Scholar 

  12. B. M. Kim, J. S. Park, J. H. Cho, Tetrahedron Lett., 2000, 41, 10031.

    Article  CAS  Google Scholar 

  13. A. Pérez-Cadenas, L. Godino-Salido, R. López-Garzón, P. Arranz-Mascarós, D. Gutiérrez-Valero, R. Cuesta-Martos, Transition Met. Chem., 2001, 26, 581.

    Article  Google Scholar 

  14. A. Pérez-Cadenas, R. López-Garzón, L. Godino-Salido, P. Arranz-Mascarós, D. Gutiérrez-Valero, T. Carillo-Márquez, Transition Met. Chem., 2002, 27, 184.

    Article  Google Scholar 

  15. L. Aurelio, R. T. C. Brownlee, A. B. Hughes, Org. Lett., 2002, 4, 3767.

    Article  CAS  Google Scholar 

  16. K. N. White, J. P. Konopelski, Org. Lett., 2005, 7, 4111.

    Article  CAS  Google Scholar 

  17. C. DalZotto, J. Michaux, E. Martinand-Lurin, J.-M. Campagne, Eur. J. Org. Chem., 2010, 3811.

    Google Scholar 

  18. B. A. Trofimov, A. G. Mal’kina, O. A. Shemyakina, A. P. Borisova, V. V. Nosyreva, O. A. Dyachenko, O. N. Kazheva, G. G. Alexandrov, Synthesis, 2007, 2641.

    Google Scholar 

  19. B. A. Trofimov, A. G. Mal’kina, O. A. Shemyakina, V. V. Nosyreva, A. P. Borisova, S. S. Khutsishvili, L. B. Krivdin, Synthesis, 2009, 3136.

    Google Scholar 

  20. B. A. Trofimov, A. G. Mal’kina, O. A. Shemyakina, V. V. Nosyreva, A. P. Borisova, A. I. Albanov, O. N. Kazheva, G. G. Alexandrov, A. N. Chekhlov, O. A. Dyachenko, Tetrahedron, 2009, 65, 2472.

    Article  CAS  Google Scholar 

  21. B. A. Trofimov, A. G. Mal’kina, A. P. Borisova, O. A. Shemyakina, V. V. Nosyreva, A. I. Albanov, Synthesis, 2010, 3174.

    Google Scholar 

  22. A. G. Mal’kina, A. P. Borisova, O. A. Shemyakina, V. V. Nosyreva, A. I. Albanov, B. A. Trofimov, ARKIVOC, 2011, Part IX, 189.

    Google Scholar 

  23. V. A. Shagun, V. I. Smirnov, L. M. Sinegovskaya, V. V. Nosyreva, A. P. Borisova, O. A. Shemyakina, A. G. Mal’kina, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 2451 [Izv. Akad. Nauk, Ser. Khim., 2011, 2405].

    Article  CAS  Google Scholar 

  24. S. R. Landor, B. Demetriou, R. Grzeskowiak, D. Pavey, J. Organomet. Chem., 1975, 93, 129.

    Article  CAS  Google Scholar 

  25. B. A. Trofimov, L. V. Andriyankova, S. I. Shaikhudinova, T. I. Kazantseva, A. G. Mal’kina, S. A. Zhivet’ev, A. V. Afonin, Synthesis, 2002, 853.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation

    A. G. Mal’kina, V. V. Nosyreva, O. A. Shemyakina, A. P. Borisova, A. I. Albanov, A. A. Tatarinova & B. A. Trofimov

Authors
  1. A. G. Mal’kina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. V. Nosyreva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. A. Shemyakina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. P. Borisova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. I. Albanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. A. Tatarinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. B. A. Trofimov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to B. A. Trofimov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences M. P. Egorov on the occasion of his 60th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2538—2543, Novemer, 2013.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mal’kina, A.G., Nosyreva, V.V., Shemyakina, O.A. et al. Chemo- and regioselective modification of l-histidine with tertiary cyanopropargylic alcohols. Russ Chem Bull 62, 2538–2543 (2013). https://doi.org/10.1007/s11172-013-0367-8

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-013-0367-8

Key words

Search

Navigation