Skip to main content
Log in

Zur Synthese von Human-Big-Gastrin I und seinem 32-Leucin-Analogon 1. Mitteilung: Darstellung der Teilsequenzen 28–34, 23–27, 21–22 und 15–20

The syntheses of Human-Big-Gastrin I and its 32-leucine-analogue I. Preparation of fragments 28–34, 23–27, 21–22 and 15–20

  • Organische Chemie und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

Human-Big-Gastrin I, a peptide hormone of 34 amino acid residues, and the 32-leucine analogue were synthesized. For this purpose six suitable peptide fragments were prepared at first, which subsequently were condensed to the total sequence. In this paper we describe the syntheses of four suitably protected peptide fragments corresponding to the sequences 28–34, 23–27, 21–22 and 15–20 of human-big-gastrin I. For the protection of the side-chain functionstert-butanol derived groups removable in the final step by acidolytic cleavage were used. The α-amino-functions were selectively blocked as benzyloxycarbonyl-and 2-nitrophenylsulfenyl-derivatives, respectively.

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

Access this article

We’re sorry, something doesn't seem to be working properly.

Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Similar content being viewed by others

Literatur

  1. Vorläufige Mitteilung:E. Wünsch, G. Wendlberger, A. Hallett, E. Jaeger, S. Knof, L. Moroder, R. Scharf, I. Schmidt, P. Thamm undL. Wilschowitz, Z. Naturforsch.32 c, 495 (1977).

    Google Scholar 

  2. Houben-Weyl, Methoden der organischen Chemie, Bd. XV (E. Wünsch, Hrsg.). Stuttgart: G. Thieme. 1974.

    Google Scholar 

  3. R. A. Gregory undH. J. Tracy, Gut5, 103 (1964).

    Google Scholar 

  4. H. J. Tracy undR. A. Gregory, Nature (London)204, 935 (1964).

    Google Scholar 

  5. R. A. Gregory, P. M. Hardy, D. S. Jones, G. W. Kenner undR. C. Sheppard, Nature (London)204, 931 (1964).

    Google Scholar 

  6. R. A. Gregory, H. J. Tracy undM. I. Grossman, Nature (London)209, 583 (1966).

    Google Scholar 

  7. J. S. Morley undJ. M. Smith, J. Chem. Soc.1968, 726.

  8. J. S. Morley, H. J. Tracy undR. A. Gregory, Nature (London)207, 1356 (1965).

    Google Scholar 

  9. G. W. Kenner, J. J. Mendive undR. C. Sheppard, J. Chem. Soc.1968, 761.

  10. E. Wünsch undK. H. Deimer, Hoppe-Seyler's Z. Physiol. Chem.353, 1246 (1972).

    Google Scholar 

  11. B. Konz, F. Holle, E. Wünsch, K. Kissler undE. Leimer, Z. Gastroent.9, 413 (1971).

    Google Scholar 

  12. J. F. Rehfeld undF. Stadil, Gut14, 369 (1973).

    Google Scholar 

  13. S. J. Chan, P. Keim undD. F. Steiner, Proc. Natl. Acad. Sci. U.S.A.73, 1964 (1976).

    Google Scholar 

  14. B. Kemper, J. F. Habener, M. D. Ernst, J. T. Potts, jr., undA. Rich, Biochemistry15, 15 (1976).

    Google Scholar 

  15. R. A. Gregory undH. J. Tracy, Gut15, 683 (1974).

    Google Scholar 

  16. R. A. Gregory, H. J. Tracy, I. Harris, M. J. Runswick, S. Moore, G. W. Kenner undR. Ramage, Hoppe-Seyler's Z. Physiol. Chem.360, 73 (1979).

    Google Scholar 

  17. R. S. Yalow undE. Straus, in: Symposium on Hormonal Receptors in Digestive Tract Physiology (S. Bonfils, P. Fromageot undG. Rosselin, Hrsg.), S. 79. Amsterdam: North Holland Publ. Co. 1977.

    Google Scholar 

  18. R. A. Gregory undH. J. Tracy, Lancet2, 797 (1972).

    Google Scholar 

  19. R. A. Gregory undH. J. Tracy, in: Gastrointestinal Hormones (J. C. Thomson, Hrsg.), S. 13. Austin: University of Texas Press. 1975.

    Google Scholar 

  20. A. M. Choudhury, G. W. Kenner, S. Moore, R. Ramage, P. M. Richards, W. D. Thorpe, L. Moroder, G. Wendlberger undE. Wünsch, in: Peptides 1976 (A. Loffet, Hrsg.), S. 257. Editions de l'Universite de Bruxelles. 1976.

  21. G. W. Kenner, Biochem. Soc. Meeting, Edinburgh, 1975.

  22. E. Wünsch, Z. Gastroent.14, 116 (1976).

    Google Scholar 

  23. E. Wünsch, G. Wendlberger undK. H. Deimer, Hoppe-Seyler's Z. Physiol. Chem.357, 447 (1976).

    Google Scholar 

  24. E. Wünsch, G. Wendlberger undH. Stocker, Hoppe-Seyler's Z. Physiol. Chem.357, 459 (1976).

    Google Scholar 

  25. E. Wünsch undG. Wendlberger, Chem. Ber.101, 3659 (1968).

    Google Scholar 

  26. E. Wünsch undG. Wendlberger, Chem. Ber.105, 2508 (1972).

    Google Scholar 

  27. L. Zervas, D. Borovas undE. Grazis, J. Amer. Chem. Soc.85, 3660 (1963).

    Google Scholar 

  28. P. Sieber undB. Iselin, Helv. Chim. Acta51, 622 (1968).

    Google Scholar 

  29. E. Wünsch, F. Drees undJ. Jentsch, Chem. Ber.98, 803 (1965).

    Google Scholar 

  30. G. W. Anderson, J. E. Zimmerman undF. M. Callahan, J. Amer. Chem. Soc.86, 1839 (1964).

    Google Scholar 

  31. E. Wünsch undF. Drees, Chem. Ber.99, 110 (1966).

    Google Scholar 

  32. F. Weygand, D. Hoffmann undE. Wünsch, Z. Naturforsch.21 b, 426 (1966).

    Google Scholar 

  33. E. Wünsch undF. Drees, Chem. Ber.100, 816 (1967).

    Google Scholar 

  34. B. Riniker, B. Kamber undP. Sieber, Helv. Chim. Acta58, 1086 (1975).

    Google Scholar 

  35. L. Moroder, F. Drees, E. Jaeger undE. Wünsch, Hoppe-Seyler's Z. Physiol. Chem.359, 147 (1978).

    Google Scholar 

  36. K. L. Agarwal, G. W. Kenner undR. C. Sheppard, J. Chem. Soc.1969, 2213.

  37. E. Wünsch undR. Spangenberg, Chem. Ber.104, 2427 (1971).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Abkürzungen: Es werden hier vorwiegend die von der IUPAC-IUB Commission on Biochemical Nomenclature empfohlenen Abkürzungen für Aminosäuren und Schutzgruppen verwendet. Wegen der universellen Anwendbarkeit bedienen sich die Autoren auch der imHouben-Weyl 2 niedergelegten und eingehend erläuterten Abkürzungen.DCCD=N,N′-Dicyclohexylcarbodiimid,HONSu=N-Hydroxysuccinimid.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wendlberger, G., Moroder, L., Hallett, A. et al. Zur Synthese von Human-Big-Gastrin I und seinem 32-Leucin-Analogon 1. Mitteilung: Darstellung der Teilsequenzen 28–34, 23–27, 21–22 und 15–20. Monatshefte für Chemie 110, 1301–1315 (1979). https://doi.org/10.1007/BF00938288

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00938288

Keywords

Navigation