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A new solid-phase synthesis of porcine vasoactive intestinal peptide using Nα-9-fluorenylmethyloxycarbonyl amino acids

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  • Chimica, Biochimica
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Summary

The solid-phase synthesis of an octacosapeptide amide corresponding to the amino acid sequence of porcine vasoactive intestinal peptide (VIP) is described. No final treatment with strong, anhydrous acid was employed, since the use of base-labile 9-fluorenylmethyloxycarbonyl amino acids bearing tert-butyl based side chain protection enabled the peptide chain assembly to be performed on p-benzyloxybenzyl amine resin, which was cleaved from the whole peptide amide at the end of the synthesis by diluted trifluoroacetic acid.

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References

  1. S. I. Said and V. Mutt, Science169, 1217 (1970).

    Article  CAS  PubMed  Google Scholar 

  2. V. Mutt and S. I. Said, Eur. J. Biochem.42, 581 (1974).

    Article  CAS  PubMed  Google Scholar 

  3. A. Nilsson, FEBS Lett.60, 322 (1975).

    Article  CAS  PubMed  Google Scholar 

  4. P. L. Rayford, T. A. Miller and J. C. Thompson, New Engl. J. Med.294, 1093 (1976).

    Article  CAS  PubMed  Google Scholar 

  5. J. M. Polak, A. G. E. Pearse, J. C. Garaud and S. R. Bloom, Gut15, 720 (1974).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. M. G. Bryant, J. M. Polak, I. Modlin, S. R. Bloom, R. H. Albuquerque, and A. G. E. Pearse, Lancet1, 991 (1976)

    Article  CAS  PubMed  Google Scholar 

  7. L. J. Larsson, J. Faharenkrug, O. S. de Muckadell, F. Sundler, R. Hakanson and J. F. Rehfield, Proc. natl Acad. Sci. USA73, 3197 (1976).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. S. I. Said and J. C. Porter, Life Sci.24, 227 (1979).

    Article  CAS  PubMed  Google Scholar 

  9. R. B. Merrifield, J. Am. chem. Soc.85, 2149 (1963).

    Article  CAS  Google Scholar 

  10. D. H. Coy and J. Gardner, Int. J. Peptide Prot. Res.15, 73 (1980).

    Article  CAS  Google Scholar 

  11. C. Tzougraki, R. C. Makofske, T. G. Gabriel, J. Michalewsky, J. Meienhofer and C. H. Li, Int. J. Peptide Prot. Res.15, 377 (1980).

    Article  CAS  Google Scholar 

  12. R. Colombo, Int. J. Peptide Prot. Res.19, 71 (1982).

    Article  CAS  Google Scholar 

  13. L. A. Carpino and G. Y. Han, J. Am. chem. Soc.92, 5748 (1970).

    Article  CAS  Google Scholar 

  14. E. Atherton, H. Fox, D. Harkiss, and R. C. Sheppard, J. chem. Soc. chem. Commun.1978, 539

  15. C.-D. Chang and J. Meienhofer, Int. J. Peptide Prot. Res.11, 246 (1978)

    Article  CAS  Google Scholar 

  16. C. D. Chang, M. Waki, M. Ahmad, J. Meienhofer, E. O. Lundell and J. D. Haug, Int. J. Peptide Prot. Res.15, 59 (1980).

    Article  CAS  Google Scholar 

  17. R. Colombo, Experientia37, 798 (1981)

    Article  CAS  Google Scholar 

  18. R. Colombo, J. chem. Soc. chem. Commun.1981, 1012.

  19. P. G. Pietta and O. Brenna, J. org. Chem.40, 2995 (1975).

    Article  CAS  PubMed  Google Scholar 

  20. L. A. Carpino and G. Y. Han, J. org. Chem.38, 4218 (1973).

    Article  Google Scholar 

  21. C.-D. Chang, A. M. Felix, M. H. Jimenez and J. Meienhofer, Int. J. Peptide Prot. Res.15, 485 (1980).

    Article  CAS  Google Scholar 

  22. E. Schnabel, J. Stoltefuss, H. A. Offe and E. Klauke, Justus Liebigs Annln Chem.743, 57 (1971).

    Article  CAS  Google Scholar 

  23. E. Kaiser, L. R. Colescott, C. D. Bossinger, and P. I. Cook, Analyt. Biochem.52, 377 (1973).

    Article  Google Scholar 

  24. A. M. Felix and M. H. Jimenez, Analyt. Biochem.52, 377 (1973).

    Article  CAS  PubMed  Google Scholar 

  25. B. S. Hartley, Biochem. J.119, 805 (1970).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. G. O. Barbezat and M. I. Grossman, Science174, 422 (1971).

    Article  CAS  PubMed  Google Scholar 

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Colombo, R. A new solid-phase synthesis of porcine vasoactive intestinal peptide using Nα-9-fluorenylmethyloxycarbonyl amino acids. Experientia 38, 773–775 (1982). https://doi.org/10.1007/BF01972263

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