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A rational approach to the synthesis of phosphonamidate peptides

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Summary

A rational approach to the synthesis of phosphonamidate pseudopeptides is described. This strategy can be easily applied to the preparation of peptides containing phosphonic acid residues at various positions, as well as sidechain-functionalized amino acid residues. The reaction conditions are compatible with the severe lability of the P-N bond, and the absence of racemization is demonstrated by31P NMR analysis. This approach is suitable for application in solid-phase synthesis of biologically active phosphonopeptides.

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References

  1. Bartlett, P.A. and Marlowe, C.K., Biochemistry, 26 (1987) 8553.

    Google Scholar 

  2. Jacobsen, N.E. and Bartlett, P.A., J. Am. Chem. Soc., 103 (1981) 654.

    Google Scholar 

  3. Mookhiar, K.A., Marlowe, C.K., Bartlett, P.A. and VanWart, H.E., Biochemistry, 26 (1987) 1962.

    Google Scholar 

  4. Hanson, J.E., Kaplan, A.P. and Bartlett, P.A., Biochemistry, 28 (1989) 6294.

    Google Scholar 

  5. Morgan, B.P., Scholtz, J.M., Ballinger, I.D., Zipkin, I.D. and Bartlett, P.A., J. Am. Chem. Soc., 113 (1991) 297.

    Google Scholar 

  6. Elliott, R.L., Marks, N., Berg, M.J. and Porthogese, P.S., J. Med. Chem., 28 (1985) 1208.

    Google Scholar 

  7. Lerner, R.A., Benkovic, S.J. and Shultz, P.G., Science, 252 (1991) 659.

    Google Scholar 

  8. Rahil, J. and Haake, P., J. Am. Chem. Soc., 103 (1981) 1723.

    Google Scholar 

  9. Gross, E. and Meinhofer, J., In Gross, E. and Meinhofer, J. (Eds.) The Peptides, Analysis, Synthesis, Biology, Vol. 1, Academic Press, London, 1972, p. 42.

    Google Scholar 

  10. Dumy, P., Escale, R., Girard, J.P., Parello, J. and Vidal, J.P., Synthesis, (1992) 1225.

  11. Kafarski, P., Lejczak, B. and Szewczyk, J., Can. J. Chem., 61 (1983) 2425.

    Google Scholar 

  12. Hoffmann, M., Synthesis, (1986) 557.

  13. Kessler, H., Griesinger, C., Zarbock, J. and Loosli, H.R., J. Magn. Reson., 57 (1984) 331.

    Google Scholar 

  14. Maffre-Lafon, D., Escale, R., Dumy, P., Vidal, J.P. and Girard, J.P., Tetrahedron Lett., 35 (1994) 4097.

    Google Scholar 

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Maffre-Lafon, D., Dumy, P., Escale, R. et al. A rational approach to the synthesis of phosphonamidate peptides. Lett Pept Sci 1, 51–55 (1994). https://doi.org/10.1007/BF00132762

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  • DOI: https://doi.org/10.1007/BF00132762

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