Synthesis of substance P partial sequential peptides on a photolytically removable 4-aminomethyl-3-nitrobenzoylaminomethyl polystyrene support
- 21 Downloads
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.
KeywordsPeptide synthesis substance P solid-phase synthesis photoremovable polymeric supports
Unable to display preview. Download preview PDF.
- Ajayaghosh A and pillai V N R 1988Proc. Indian Acad. Sci. (Chem. Sci.) 100 389Google Scholar
- Barany G and Merrifield R B 1979The peptides (eds) E Gross and J Meienhofer (New York: Academic Press) vol. 2, p. 1Google Scholar
- Beyerman H C, Hindricks H and de Leer E W B 1968J. Chem. Soc., Chem. Commun. 1668Google Scholar
- Bodanszky M and Sheehan J C 1966Chem. Ind. (London) 1597Google Scholar
- Giralt E, Albericio F, Pedroso E, Granier C and Van Rietschotten J 1982Tetrahedron 40 4313Google Scholar
- Izeboud E and Beyerman H C 1978Recl. Trav. Chim. Pays-Bas 1 1Google Scholar
- Pillai V N R 1987Organic photochemistry (ed.) A Padwa (New York: Marcel Dekker) vol. 9, p. 224Google Scholar
- Pillai V N R and Mutter M 1982Top. Curr. Chem. 106 119Google Scholar
- Rich D H and Gurwara S K 1975aTetrahedron Lett. 301Google Scholar