Skip to main content
SpringerLink
Log in

Reactive intermediates in peptide synthesis: Molecular and crystal structures of HOAt and HOOBt, and some ester and amide derivatives of HOBt, HOAt and HOOBt

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

Summary

X-ray diffraction structure determinations of HOAt and HOOBt, two well-known additives for peptide bond formation, are reported in conjunction with those of seven derivatives of HOBt, HOAt, and HOOBt, five of which originate from Nα-protected α-amino acids. In the crystal state the two additives are found in the 1-hydroxy tautomeric form. In contrast to six derivatives which crystallize as esters, one, Fmoc-(N)OBt, is observed in the isomeric amide-type (urethane) form.

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. Toniolo, C., Crisma, M. and Formaggio, F., Biopolymers (Pept. Sci.), 40 (1996) 627.

    Article  CAS  Google Scholar 

  2. König, W. and Geiger, R., Chem. Ber., 103 (1970) 788.

    PubMed  Google Scholar 

  3. Knorr, R., Trzeciak, A., Bannwarth W. and Gillessen, D., Tetrahedron Lett., (1989) 1927.

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

    Article  CAS  Google Scholar 

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

  6. König, W. and Geiger, R., Chem. Ber., 103 (1970) 2024.

    PubMed  Google Scholar 

  7. König, W. and Geiger, R., Chem. Ber., 103 (1970) 2034.

    PubMed  Google Scholar 

  8. Atherton, E., Cameron, L., Meldal, M. and Sheppard, R., J. Chem. Soc., Chem. Commun., (1986) 1763.

  9. Akaji, K., Kuriyama, N. and Kiso, Y., Tetrahedron Lett, 35 (1994) 3315.

    Article  CAS  Google Scholar 

  10. Bosch, R., Jung, G. and Winter, W., Acta Crystallogr., C 39 (1983) 1089.

    Article  Google Scholar 

  11. Pfister-Guillouzo, G., Gracian, F., Paez, J.A., Garcia-Gomez, C. and Elguero, J., Spectrochim. Acta, A51 (1995) 1801.

    Article  Google Scholar 

  12. Vlassi, M., Germain, M., Barlos, K., Mamos, P. and Refaat, L.S., Z. Kristallogr., 192 (1990) 59.

    CAS  Google Scholar 

  13. McCarthy, D.G., Hegarty, A.F. and Hathaway, B.J., J. Chem. Soc., Perkin Trans. 2 (1977) 224.

    Google Scholar 

  14. Barlos, K., Papaioannu, D., Voliotis, S., Prewo, R. and Bieri, J.H., J. Org. Chem., 50 (1985) 696.

    Article  CAS  Google Scholar 

  15. Sliedregt, K.M., Schouten, A., Kroon, J. and Liskamp, R.M.J., Tetrahedron Lett., 37 (1996) 4237.

    Article  CAS  Google Scholar 

  16. Singh, J., Fox, R., Wong, M., Kissick, T.P., Moniot, J.L., Gougoutas, J.Z., Malley, M.F. and Kocy, O., J. Org. Chem., 53 (1988) 205.

    Article  CAS  Google Scholar 

  17. Nagarajan, S., Wilson, S.R. and Rinehart Jr., K.J., J. Org. Chem., 50 (1985) 2174.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  19. Henklein, P., Costisella, B., Wray, V., Domke, T., Carpino, L.A., El-Faham, A., Kates, S.A., Abdelmoty, I. and Foxman, B.M., In Ramage, R. and Epton, R. (Eds.) Peptides 1996, Mayflower Worldwide, Kingswinford, U.K., 1998, in press.

  20. Leplawy, M.T., Jones, D.S., Kenner, G.W. and Sheppard, R.C., Tetrahedron, 11 (1960) 39.

    Article  CAS  Google Scholar 

  21. Crisma, M., Moretto, V., Valle, G., Formaggio, F. and Toniolo, C., Int. J. Pept. Protein Res., 42 (1993) 378.

    Article  PubMed  CAS  Google Scholar 

  22. Paquet, A., Can. J. Chem., 60 (1982) 976.

    Article  CAS  Google Scholar 

  23. Sheldrick, G.M., SHELXS 86, Program for the Solution of Crystal Structures, University of Göttingen, Göttingen, Germany, 1986.

    Google Scholar 

  24. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. and Camalli, M., J. Appl. Crystallogr., 27 (1994) 435.

    Article  Google Scholar 

  25. Sheldrick, G.M., SHELX 76, Program for Crystal Structure Determination, University of Cambridge, Cambridge, U.K., 1976.

    Google Scholar 

  26. Allen, F.A., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G. and Taylor, R., J. Chem. Soc., Perkin Trans. 2, (1987) S1.

    Google Scholar 

  27. Ramakrishnan, C. and Prasad, N., Int. J. Protein Res., 3 (1971) 209.

    CAS  Google Scholar 

  28. Taylor, R., Kennard, O. and Versichel, W., Acta Crystallogr., B40 (1984) 280.

    Article  Google Scholar 

  29. Görbitz, C.M., Acta Crystallogr., B45 (1989) 390.

    Article  Google Scholar 

  30. Brown, I.D., Acta Crystallogr., A32 (1976) 24.

    Article  Google Scholar 

  31. Mitra, J. and Ramakrishnan, C., Int. J. Pept. Protein Res., 9 (1977) 27.

    Article  PubMed  CAS  Google Scholar 

  32. Toniolo, C. and Benedetti, E., Macromolecules, 24 (1991) 4004.

    Article  CAS  Google Scholar 

  33. Toniolo, C., Crisma, M., Formaggio, F., Valle, G., Cavicchioni, G., Précigoux, G., Aubry, A. and Kamphuis, J., Biopolymers, 33 (1993) 1061.

    Article  CAS  Google Scholar 

  34. Nyburg, S.C. (Ed.) X-Ray Analysis of Organic Structures, Academic Press, New York, NY, 1961.

    Google Scholar 

  35. Llamas Saiz, A.L. and Foces-Foces, C., J. Mol. Struct., 238 (1990) 367.

    Article  CAS  Google Scholar 

  36. Carpino, L.A., El-Faham, A. and Albericio, F., J. Org. Chem., 60 (1995) 3561.

    Article  CAS  Google Scholar 

  37. Johnson, C.K., ORTEP II. Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, 1976.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Biopolymer Research Centre, CNR, Department of Organic Chemistry, University of Padova, I-35131, Padova, Italy

    Marco Crisma, Giovanni Valle, Vittorio Moretto, Fernando Formaggio & Claudio Toniolo

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

    Fernando Albericio

Authors
  1. Marco Crisma
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Giovanni Valle
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Vittorio Moretto
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Fernando Formaggio
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Claudio Toniolo
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. 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

Crisma, M., Valle, G., Moretto, V. et al. Reactive intermediates in peptide synthesis: Molecular and crystal structures of HOAt and HOOBt, and some ester and amide derivatives of HOBt, HOAt and HOOBt. Lett Pept Sci 5, 247–258 (1998). https://doi.org/10.1007/BF02443541

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02443541

Key words

Search

Navigation