The cyclic dermorphin analogues, containing a carbonyl bridge have already been published [1-3];  all of them were N-unsubstituted amides.

The object of this study was the synthesis of N-substituted amides of dermorphin cyclic analogues containing an ureido group (Formula I) in the hope of preparing more proteolytical stable and analgesic active peptides.

For the synthesis of N-substituted amides both approaches were used: solid phase peptide synthesis (SPPS) and classical method in solution. SPPS was carried out on functionalized MBH-resin [4] whereas classical metod was found to be more convenient to prepare a series of differently substituted amides starting from a common synton(s). All analogues were purified by semi-preparative HPLC metod.

REFERENCES

1. Filip K., Oleszczuk M., Pawlak D., Wójcik J., Chung N.N., Schiller P.W., Izdebski J. Potent side-chain to side-chain cyclized dermorphin analogues containing a carbonyl bridge. J. Peptide Sci. 2003; 9: 649–657.

2. Filip K., Oleszczuk M., Wójcik J., Chung N.N., Schiller P.W., Pawlak D., Zieleniak A., Parcińska A., Witkowska E., Izdebski J. Cyclic enkephalin and dermorphin analogues containing a carbonyl bridge. J. Peptide Sci. 2005; 11: 347–352.

3. Witkowska E., Nowakowski M., Oleszczuk M., Filip K., Ciszewska M., Chung N.N., Schiller P.W., Wójcik J., Izdebski J. Ureido group containing cyclic dermorphin(1–7) analogues: synthesis, biology and conformation. J. Peptide Sci. 2007; 13: 519–528.

4. A. Wiszniewska, D. Kunce, N.N. Chung, P.W. Schiller, J. Izdebski, 2003; Synthesis of peptido­mimetics: An evaluation of p-nitrophenyl carbamate of ethylenediamine,  Lett .Pept. Sci. 10:33-39

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