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Convenient syntheses of phosphinic analogues of γ-aminobutyric- and glutamic acids

Russian Journal of Bioorganic Chemistry volume 42, pages 672–676 (2016)Cite this article

Abstract

Three-steps, one-pot synthesis of 2-amino-4-(hydroxyphosphinyl)butyric acid from dibutyl ester of vinylphosphinic acid was carried out with an overall yield of 66%. 3-Aminopropylphosphinic acid was prepared from allylamine in three steps with an overall yield of 56%. These improved protocols allowed to obtain these commercially unavailable phosphinic analogues of glutamic acid and GABA for testing on potential molecular targets.

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Abbreviations

GABA:

4-aminobutyric acid

GABA-P H :

3-aminopropylphosphinic acid

Glu-γ-P H :

2-amino-4-(hydroxyphosphinyl) butyric acid

AIBN:

α,α',-azoisobutyronitrile

PT:

phosphinotricin, 2-amino-4-(hydroxymethylphosphinyl)butyric acid

References

  1. Kukhar, V.P. and Hudson, H.R., Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity, Wiley, 2000.

    Google Scholar 

  2. Khurs, E.N., Osipova, T.I., and Khomutov, R.M, Bioorg. Khim., 1989, vol. 15, pp. 552–555.

    CAS  PubMed  Google Scholar 

  3. Laber, B. and Amrhein, N, Biochem. J., 1987, vol. 248, pp. 351–358.

    CAS  Article  PubMed  PubMed Central  Google Scholar 

  4. Khomutov, R.M., Khurs, E.N., Dzhavahia, V.G., Voinova, T.M., and Ermolinsky, B.S, Bioorg. Khim., 1987, vol. 13, pp. 1422–1424.

    CAS  Google Scholar 

  5. Biryukov, A.I., Osipova, T.I., and Khomutov, R.M., FEBS Lett., 1978, vol. 91, pp. 246–248.

    CAS  Article  PubMed  Google Scholar 

  6. Faleev, N.G., Alferov, K.V., Tsvetikova, M.A., Morozova, E.A., Revtovich, S.V., Khurs, E.N., Vorob’ev, M.M., Phillips, R.S., Demidkina, T.V., and Khomutov, R.M, Biochim. Biophys. Acta, 2009, vol. 1794, pp. 1414–1420.

    CAS  Article  PubMed  Google Scholar 

  7. Faleev, N.G., Zhukov, Yu.N., Khurs, E.N., Gogoleva, O.I., Barbolina, M.V., Bazhulina, N.P., Belikov, V.M., Demidkina, T.V., and Khomutov, R.M, Eur. J. Biochem., 2000, vol. 267, pp. 6897–6902.

    CAS  Article  PubMed  Google Scholar 

  8. Schulz, A., Taggeselle, P., Tripier, D., and Bartsch, K, Appl. Environ. Microbiol., 1990, vol. 56, pp. 1–6.

    CAS  PubMed  PubMed Central  Google Scholar 

  9. Laber, B. and Amrhein, N, Biochem. J., 1987, vol. 248, pp. 351–358.

    CAS  Article  PubMed  PubMed Central  Google Scholar 

  10. Schonbrunn-Hanebeck, E., Laber, B., and Amrhein, N, Biochemistry, 1990, vol. 29, pp. 4880–4885.

    CAS  Article  PubMed  Google Scholar 

  11. Duncan, K. and Walsh, C.T, Biochemistry, 1988, vol. 27, pp. 3709–3714.

    CAS  Article  PubMed  Google Scholar 

  12. Badet, B., Inagaki, K., Soda, K., and Walsh, C.T, Biochemistry, 1986, vol. 25, pp. 3275–3282.

    CAS  Article  PubMed  Google Scholar 

  13. Badet, B. and Walsh, C, Biochemistry, 1985, vol. 24, pp. 1333–1341.

    CAS  Article  PubMed  Google Scholar 

  14. Allen, J.G., Atherton, F.R., Hall, M.J., Hassall, C.H., Holmes, S.W., Lambert, R.W., Nisbet, L.J., and Ringrose, P.S, Nature, 1978, vol. 272, pp. 56–58.

    CAS  Article  PubMed  Google Scholar 

  15. Seto, H., Sasaki, T., Imay, S., Tsuruoka, T., Ogawa, H., Satoh, A., Inouye, S., Niida, T., and Otake, N., J. Antibiot., 1983, vol. 36. pp. 96–98.

    CAS  Article  PubMed  Google Scholar 

  16. Imai, S., Seto, H., Sasaki, T., Tsuroukai, T., Ogawa, H., Satoh, A., Inouye, S., Niida, T., and Otake, N., J. Antibiot., 1985, vol. 38, pp. 687–690.

    CAS  Article  PubMed  Google Scholar 

  17. Selvam, C., Goudet, C., Oueslati, N., Pin, J.P., and Acher, F.C., J. Med. Chem., 2007, vol. 50, pp. 4656–4664.

    CAS  Article  PubMed  Google Scholar 

  18. Maier, L. and Rist, G, Phosph. Sulfur, 1983, vol. 17, pp. 21–28.

    CAS  Article  Google Scholar 

  19. Kabachnik, M.I, Zhun-yui Ch., and Tsvetkov E.N, Zh. Obshch. Khim., 1962, vol. 32, pp. 3351–3360.

    CAS  Google Scholar 

  20. Baylis, E.K., Campbell, C.D., and Dingwall, J.G., J. Chem. Soc, Perkin Trans. 1, 1984, pp. 2845–2853.

    Google Scholar 

  21. Dingwall, J.G., Ehrenfreund, J., and Hall, R.G, Tetrahedron, 1989, vol. 45, pp. 3787–3808.

    CAS  Article  Google Scholar 

  22. Gallagher, M.J. and Honegger, H, Aust. J. Chem., 1980, vol. 33, pp. 287–294.

    CAS  Article  Google Scholar 

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Authors and Affiliations

  1. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, ul. Vavilova 32, Moscow, 119991, Russia

    M. A. Khomutov, S. N. Kochetkov & A. R. Khomutov

  2. Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, Moscow, 117997, Russia

    A. A. Formanovsky & I. V. Mikhura

  3. School of Pharmacy, University of Eastern Finland, Kuopio, FIN-70211, Finland

    J. Vepsalainen

  4. Istituto Pasteur Italia–Fondazione Cenci Bolognetti, Department of Medico-Surgical Sciences and Biotechnologies, Sapienza University of Rome, Corso della Repubblica 79, Latina, 04100, Italy

    D. De Biase

Authors
  1. M. A. Khomutov
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  2. A. A. Formanovsky
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  3. I. V. Mikhura
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  4. J. Vepsalainen
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  5. S. N. Kochetkov
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  6. D. De Biase
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  7. A. R. Khomutov
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Corresponding authors

Correspondence to D. De Biase or A. R. Khomutov.

Additional information

Original Russian Text © M.A. Khomutov, A.A. Formanovsky, I.V. Mikhura, J. Vepsalainen, S.N. Kochetkov, D. De Biase, A.R. Khomutov, 2016, published in Bioorganicheskaya Khimiya, 2016, Vol. 42, No. 6, pp. 741–745.

The article was translated by the authors.

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Khomutov, M.A., Formanovsky, A.A., Mikhura, I.V. et al. Convenient syntheses of phosphinic analogues of γ-aminobutyric- and glutamic acids. Russ J Bioorg Chem 42, 672–676 (2016). https://doi.org/10.1134/S1068162016060042

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  • DOI: https://doi.org/10.1134/S1068162016060042

Keywords

  • amino acids
  • phosphorus analogues
  • glutamic acid
  • γ-aminobutyric acid (GABA)