Synthesis of substance P partial sequential peptides on a photolytically removable 4-aminomethyl-3-nitrobenzoylaminomethyl polystyrene support

  • V K Haridasan
  • V N Rajasekharan Pillai


Sequential peptides corresponding to substance P (6–11) were synthesised on a photocleavable 4-aminomethyl-3-nitrobenzoylaminomethyl polystyrene resin. This photoremovable polymeric support, useful for the synthesis of C-terminal peptide amides, was prepared from 4-bromomethyl-3-nitrobenzoylaminomethyl polystyrene by treatment with potassium phthalimide followed by hydrazinolysis. Amino acid residues were incorporated onto this support following the standard solid-phase methodology of peptide synthesis. The protected peptide amides were cleaved from the resin by photolysis with light of wavelength 350 nm. The resin was used for the synthesis of peptides including the partial sequence corresponding to substance P (9–11) which was further subjected to stepwise synthesis to prepare substance P (6–11) in an overall yield of 88%. This approach combines the advantages of the photochemical deprotection of the 4-aminomethyl-3-nitro carboxyl protecting group, the polymer-supported peptide synthesis and the polymer-analogous functionalisation procedure to obtain the C-terminal peptide amide under mild conditions.


Peptide synthesis substance P solid-phase synthesis photoremovable polymeric supports 


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  1. Ajayaghosh A and Pillai V N R 1987J. Org. Chem. 52 2714CrossRefGoogle Scholar
  2. Ajayaghosh A and pillai V N R 1988Proc. Indian Acad. Sci. (Chem. Sci.) 100 389Google Scholar
  3. Albericio F, Nicoloas E, Josa J, Grands A, Pedroso E, Giralt E, Granier C and Van Rietschotten J 1987Tetrahedron 43 5961CrossRefGoogle Scholar
  4. Barany G and Albericio F 1985J. Am. Chem. Soc. 107 4936CrossRefGoogle Scholar
  5. Barany G and Merrifield R B 1979The peptides (eds) E Gross and J Meienhofer (New York: Academic Press) vol. 2, p. 1Google Scholar
  6. Bellof D and Mutter M 1984Polym. Bull. 11 49CrossRefGoogle Scholar
  7. Beyerman H C, Hindricks H and de Leer E W B 1968J. Chem. Soc., Chem. Commun. 1668Google Scholar
  8. Bodanszky M and Sheehan J C 1966Chem. Ind. (London) 1597Google Scholar
  9. Chambers R W and Carpenter F H 1955J. Am. Chem. Soc. 77 1522CrossRefGoogle Scholar
  10. Gisin B F 1972Anal. Chim. Acta 58 248CrossRefGoogle Scholar
  11. Giralt E, Albericio F, Pedroso E, Granier C and Van Rietschotten J 1982Tetrahedron 40 4313Google Scholar
  12. Giralt E, Eritja R, Pedroso E, Granier C and Van Rietschotten J 1986Tetrahedron 42 691CrossRefGoogle Scholar
  13. Hancock W S, Prescott D J, Vagelos P R and Marshall G R 1973J. Org. Chem. 38 774CrossRefGoogle Scholar
  14. Izeboud E and Beyerman H C 1978Recl. Trav. Chim. Pays-Bas 1 1Google Scholar
  15. Kaiser E, Colescott R L, Bossinger C D and Cook P I 1970Anal. Biochem. 34 595CrossRefGoogle Scholar
  16. Manning M 1968J. Am. Chem. Soc. 90 1348CrossRefGoogle Scholar
  17. Maser F, Bode K, Pillai V N R and Mutter M 1984Adv. Polym. Sci. 65 177CrossRefGoogle Scholar
  18. Merrifield R B 1963J. Am. Chem. Soc. 85 2149CrossRefGoogle Scholar
  19. Merrifield R B 1986Science 232 341CrossRefGoogle Scholar
  20. Mitchell A R and Merrifield R B 1976J. Org. Chem. 41 2015CrossRefGoogle Scholar
  21. Orlowski R C, Walter R and Winkler D 1976J. Org. Chem. 41 3701CrossRefGoogle Scholar
  22. Penke B and Rivier J 1987J. Org. Chem. 52 1197CrossRefGoogle Scholar
  23. Pillai V N R 1987Organic photochemistry (ed.) A Padwa (New York: Marcel Dekker) vol. 9, p. 224Google Scholar
  24. Pillai V N R and Mutter M 1982Top. Curr. Chem. 106 119Google Scholar
  25. Rich D H and Gurwara S K 1975aTetrahedron Lett. 301Google Scholar
  26. Rich D H and Gurwara S K 1975bJ. Am. Chem. Soc. 97 1575CrossRefGoogle Scholar
  27. Rivier J, Vale W, Monahan M, Ling N and Burgus R 1972J. Med. Chem. 15 479CrossRefGoogle Scholar
  28. Schally A V, Arimura A, Baba Y, Nair R M G, Matsuo H, Redding T W, Debaljuk L and White W F 1971Biochem. Biophys. Res. Commun. 43 393CrossRefGoogle Scholar
  29. Takashima H, du Vigneaud V and Merrifield R B 1968J. Am. Chem. Soc. 90 1323CrossRefGoogle Scholar
  30. Tjoeng F S, Tong E K and HodgesR S 1978J. Org. Chem. 43 4190CrossRefGoogle Scholar

Copyright information

© Indian Academy of Sciences 1991

Authors and Affiliations

  • V K Haridasan
    • 1
  • V N Rajasekharan Pillai
    • 1
  1. 1.School of Chemical SciencesMahatma Gandhi UniversityKottayamIndia

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