Skip to main content
SpringerLink
Log in

Rearrangement of Glu(OtBu)- and Asp(OtBu)-containing peptides upon fluoride treatment in solid-phase synthesis

  • Published:
Letters in Peptide Science Aims and scope Submit manuscript

Summary

Although fluoride-labile protecting groups and linkers have been developed in solid-phase peptide synthesis to add an extra level of orthogonality, fluoride ions were found to convert α-peptides to their corresponding γ- or β-peptides in Glu(OtBu)- and Asp(OtBu)-containing peptidyl resins. Different peptide sequences and fluoride reagents were examined to determine the scope of this side reaction. CZE analysis was found to be a useful analytical technique to characterize peptides with respect to this phenomenon.

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. Fields, G.B., Tian, Z. and Barany, G., In Grant, G.A. (Ed.) Synthetic Peptides, A Users Guide, Freeman, New York, NY, 1992, pp. 77–183.

    Google Scholar 

  2. Barany, G. and Albericio, F., J. Am. Chem. Soc., 107 (1985) 4936.

    Google Scholar 

  3. For a recent review, see: Lloyd-Williams, P., Albericio, F. and Giralt, E., Tetrahedron, 49 (1993) 11065.

    Google Scholar 

  4. Kates, S.A., Solé, N.A., Johnson, C.R., Hudson, D., Barany, G. and Albericio, F., Tetrahedron Lett., 34 (1993) 1549.

    Google Scholar 

  5. Kates, S.A., Daniels, S.B. and Albericio, F., Anal. Biochem., 212 (1993) 303.

    Google Scholar 

  6. de laTorre, B.G., Aviño, A., Tarrason, G., Piulats, J., Albericio, F. and Eritija, R., Tetrahedron Lett., 35 (1994) 2733.

    Google Scholar 

  7. Kates, S.A., de laTorre, B.G., Eritja, R. and Albericio, F., Tetrahedron Lett., 35 (1994) 1033 and references cited therein.

    Google Scholar 

  8. Mullen, D.G. and Barany, G., Tetrahedron Lett., 28 (1987) 491.

    Google Scholar 

  9. Ramage, R., Barron, C.A., Bielecki, S. and Thomas, D.W., Tetrahedron Lett., 28 (1987) 4105.

    Google Scholar 

  10. Mullen, D.G. and Barany, G., J. Org. Chem., 53 (1988) 5240.

    Google Scholar 

  11. Carpino, L.A., Tsao, J.-H., Ringsdorf, H., Fell, E. and Hettrich, G., J. Chem. Soc., Chem. Commun., (1978) 358.

  12. Ramage, R., Barron, C.A., Bielecki, S., Holden, R. and Thomas, D.W., Tetrahedron Lett., 48 (1992) 499.

    Google Scholar 

  13. Ueki, M., Kai, K., Amemiya, M., Horino, H. and Oyamada, H., J. Chem Soc., Chem. Commun., (1988) 414.

  14. Ueki, M., Kai, K., Horino, H. and Oyamada, H., In Jung, G. and Bayer, E. (Eds.) Peptides 1988 (Proceedings of the 20th European Peptide Symposium), Walter de Gruyter, Berlin, 1989, pp. 145–147.

    Google Scholar 

  15. Ueki, M., Horino, H., Senon, C., Sakata, T. and Oyamada, H., In Yanaihara, N. (Ed.) Peptide Chemistry 1989, Protein Research Foundation, Osaka, 1990, pp. 23–28.

    Google Scholar 

  16. Nicolás, E., Pedroso, E. and Giralt, E., Tetrahedron Lett., 30 (1989) 497.

    Google Scholar 

  17. Dölling, R., Beyermann, M., Haenel, J., Kernchen, F., Krause, E., Franke, P., Brudel, M. and Bienert, M., J. Chem. Soc., Chem. Commun., (1994) 853.

  18. Chao, H.-G., Bernatowicz, M.S. and Matsueda, G.R., J. Org. Chem., 58 (1993) 2640.

    Google Scholar 

  19. Chao, H.-G., Bernatowicz, M.S., Reiss, P.D., Klimas, C.E. and Matsueda, G.R., J. Am. Chem. Soc., 116 (1994) 1746.

    Google Scholar 

  20. Sieber, P., Helv. Chim. Acta, 60 (1977) 2711.

    Google Scholar 

  21. Ueki, M. and Ameniya, M., Tetrahedron Lett., 28 (1987) 6617.

    Google Scholar 

  22. Ueki, M., Nishigaki, N., Aoki, H., Tsurusaki, T. and Katoh, T., Chem. Lett., (1993) 721.

  23. Albericio, F., Nicolás, E., Rizo, J., Ruiz-Gayo, M., Pedroso, E. and Giralt, E., Synthesis, (1990) 119.

  24. Jiang, J., Li, W.-R. and Joullié, M.M., Synth. Commun., 24 (1994) 187.

    Google Scholar 

  25. Kiso, Y., Kimura, T., Fujiwara, Y., Shimokura, M. and Nishitani, A., Chem. Pharm. Bull., 36 (1988) 5024.

    Google Scholar 

  26. Namikoshi, M., Kundu, B. and Rinehart, K.L., J. Org. Chem., 56 (1991) 5464.

    Google Scholar 

  27. Yang, Y., Sweeney, W.V., Schneider, K., Thötqvist, S., Chait, B.T. and Tam, J.P., Tetrahedron Lett., 35 (1994) 9689.

    Google Scholar 

  28. Carpino, L.A., J. Am. Chem. Soc., 115 (1993) 4397.

    Google Scholar 

  29. Carpino, L.A., El-Faham, A., Minor, C. and Albericio, F., J. Chem. Soc., Chem. Commun., (1994) 201.

  30. Carpino, L.A., El-Faham, A. and Albericio, F., Tetrahedron Lett., 35 (1994) 2279.

    Google Scholar 

  31. Angell, Y.M., García-Echeverría, C. and Rich, D.H., Tetrahedron Lett., 35 (1994) 5981.

    Google Scholar 

  32. Abdelmoty, I., Albericio, F., Carpino, L.A., Foxman, B.M. and Kates, S.A., Lett. Pept. Sci., 1 (1994) 57.

    Google Scholar 

  33. Smith, S.C., Strasters, J.K. and Khaledi, M.G., J. Chromatogr., 559 (1991) 57.

    Google Scholar 

  34. Anisfeld, S.T. and LansburyJr., P.T., J. Org. Chem., 55 (1990) 5560.

    Google Scholar 

  35. This reagent provided a third level of orthogonality in solid-phase oligonucleotide synthesis: Kremsky, J.N. and Sinha, N.D., Bioorg. Med. Chem. Lett., 4 (1994) 2171.

    Google Scholar 

  36. Quibell, M., Owen, D., Packman, L.C. and Johnson, T., J. Chem. Soc., Chem. Commun., (1994) 2343.

  37. Bidlingmeyer, B.A., Cohen, S.A. and Tarvin, T.L., J. Chromatogr., 336 (1984) 93.

    Google Scholar 

  38. Barany, G., Albericio, F., Solé, N.A., Griffin, G.W., Kates, S.A. and Hudson, D., In Schneider, C.H. and Eberle, A.N. (Eds.) Peptides 1992 (Proceedings of the 22nd European Peptide Symposium), ESCOM, Leiden, 1993, pp. 267–268.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Biosearch Division of PerSeptive Biosystems, 75A Wiggins Avenue, 01730, Bedford, MA, U.S.A.

    Steven A. Kates & Fernando Albericio

  2. Department of Organic Chemistry, University of Barcelona, E-08028, Barcelona, Spain

    Fernando Albericio

Authors
  1. Steven A. Kates
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Fernando Albericio
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kates, S.A., Albericio, F. Rearrangement of Glu(OtBu)- and Asp(OtBu)-containing peptides upon fluoride treatment in solid-phase synthesis. Lett Pept Sci 1, 213–220 (1995). https://doi.org/10.1007/BF00127267

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00127267

Key words

Search

Navigation