Skip to main content
Log in

Synthesis of phosphinic acids on the basis of hypophosphites: IV. Synthesis of pseudo-γ-glutamylglycine and its enantiomers

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

Abstract

A new method for construction of pseudopeptide molecules is proposed, exemplified by the synthesis of [3-amino-3-(hydroxycarbonyl)propyl][2-(hydroxycabonyl)ethyl]phosphinic acid (I) (pseudo-γ-glutamylglycine), starting from ammonium hypophosphite. Enzymatic synthesis using immobilized penicillamidase allowed preparation of the enantiomers of acid I.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

REFERENCES

  1. Rozhko, L.F. and Ragulin, V.V., Zh. Obshch. Khim., 2004, vol. 74, no.7, p. 1177.

    Google Scholar 

  2. Collinsova, M. and Jiracek, J., Curr. Med. Chem., 2000, vol. 7, no.6, p. 629.

    Google Scholar 

  3. Malachowski, W.P. and Coward, J.K., J. Org. Chem., 1994, vol. 59, no.25, p. 7625.

    Google Scholar 

  4. Zeng, B., Wong, K.K., Pompliano, D.L., Reddy, S., and Tanner, M.E., J. Org. Chem., 1998, vol. 63, no.26, p. 10081.

    Google Scholar 

  5. Georgiadis, D., Matziari, M., Vassiliou, S., Dive, V., and Yiotakis, A., Tetrahedron, 1999, vol. 55, no.8, p. 14635.

    Google Scholar 

  6. Buchardt, J., Ferreras, M., Krog-Jensen, C., Delaisse, J.-M., Foged, N.T., and Meldal, M., Chem. Eur. J., 1999, vol. 5, no.10, p. 2877.

    Google Scholar 

  7. Chen, H., Noble, F., Mothe, A., Meudal, H., Coric, P., Danasci-mento, S., Roques, B.P., George, P., and Fournie-Zaluski, M.-C., J. Med. Chem., 2000, vol. 43, no.7, p. 1398.

    Google Scholar 

  8. Georgiadis, D., Matziari, M., and Yiotakis, A., Tetrahedron, 2001, vol. 57, no.3, p. 3471.

    Google Scholar 

  9. Baylis, E.K., Campbell, C.D., and Dingwall, J.G., J. Chem. Soc., Perkin Trans. 1, 1984, p. 2845.

  10. McCleery, P.P. and Tuck, B., J. Chem. Soc., Perkin Trans. 1, 1989, p. 1319.

  11. Boyd, E.A., Regan, A.C., and James, K., Tetrahedron Lett., 1992, vol. 33, no.3, p. 813.

    Google Scholar 

  12. Kurdyumova, N.R., Rozhko, L.F., Ragulin, V.V., and Tsvetkov, E.N., Zh. Obshch. Khim., 1997, vol. 67, no.12, p. 1965.

    Google Scholar 

  13. Kurdyumova, N.R., Ragulin, V.V., and Tsvetkov, E.N., Mendeleev Commun., 1997, no. 2, p. 69.

  14. Ragulin, V.V. and Tsvetkov, E.N., Izv. Akad. Nauk SSSR, Ser. Khim., 1988, no. 11, p. 2652.

  15. Ragulin, V.V., Kurdyumova, N.R., and Tsvetkov, E.N., Phosphorus, Sulfur Silicon, 1994, vol. 88, nos.3, 4, p. 271.

    Google Scholar 

  16. Kurdyumova, N.R., Ragulin, V.V., and Tsvetkov, E.N., Zh. Obshch. Khim., 1994, vol. 64, no.3, p. 419.

    Google Scholar 

  17. Kurdyumova, N.R., Ragulin, V.V., and Tsvetkov, E.N., Zh. Obshch. Khim., 1996, vol. 66, no.5, p. 769.

    Google Scholar 

  18. Kurdyumova, N.R. and Ragulin, V.V., Zh. Obshch. Khim., 1999, vol. 69, no.7, p. 1126.

    Google Scholar 

  19. Voronkov, M.G. and Marmur, L.Z., Zh. Obshch. Khim., 1970, vol. 40, no.9, p. 2135.

    Google Scholar 

  20. Issleib, K., Mogelin, W., and Balszuweit, A., Z. Anorg. Allg. Chem., 1985, vol. 530, no.1, p. 16.

    Google Scholar 

  21. JP Patent 18 568, Chem. Abstr., 2001, no. 552 806.

  22. Ragulin, V.V., Zh. Obshch. Khim., 2001, vol. 71, no.11, p. 1928.

    Google Scholar 

  23. JP Patent 18 568, Chem. Abstr., 2001, no. 574 226.

  24. Rozhko, L.F., Klochkov, S. G.,, Ragulin, V.V., and Tsvetkov, E.N., Zh. Obshch. Khim., 1999, vol. 69, no.7, p. 1134.

    Google Scholar 

  25. Solodenko, V.A., Kasheva, N.A., Kukhar, V.P., Kozlova, E.V., Mironenko, D.A., and Svedas, V.-K., Tetrahedron, 1991, vol. 47, no.24, p. 3989.

    Google Scholar 

  26. Schotten, C., Ber., 1884, vol. 17, p. 2544; Baumann, E., Ber., 1886, vol. 19, p. 3218.

    Google Scholar 

  27. Valiaeva, N., Bartley, D., Konno, T., and Coward, J.K., J. Org. Chem., 2001, vol. 66, no.15, p. 5146.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Zhurnal Obshchei Khimii, Vol. 74, No. 8, 2004, pp. 1273–1278.

Original Russian Text Copyright © 2004 by Ragulin.

For communication III, see [1].

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ragulin, V.V. Synthesis of phosphinic acids on the basis of hypophosphites: IV. Synthesis of pseudo-γ-glutamylglycine and its enantiomers. Russ J Gen Chem 74, 1177–1181 (2004). https://doi.org/10.1007/s11176-005-0133-1

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11176-005-0133-1

Keywords

Navigation