Peptide synthesis depends on the proper combination of protecting groups and the right choice of the coupling method. An optimal coupling reagent should be valid for a wide variety of peptide sequences. It should be soluble and stable in the solvents used for peptide synthesis, efficient in terms of yield, minimize the racemization.

General method of preparation of stable N-triazinylammonium salts opened access to family of N-triazinylammonium sulfonates [1]. Sulfonates of N-triazinylammonium salts consist the family of inexpensive and environmentally friendly Triazine-Based Coupling Reagents. A broad variety of N-triazinylammonium sulfonates can be obtained by treatment of 2-chloro-4,6-disubstituted1,3,5-triazines with sulfonates of tertiary amines.

Up to now, we demonstrated that they can be useful for activation of carboxylic components, with activation rate depending on the structure of the tertiary amine component and sulfonic acid counterion. Participation of triazine “superactive ester”, as fundamental intermediate in condensation step, has been proved in model experiments [2]. Herein, we present the studies on screening of family of N-trizainylammonium sulfonates in peptide bond formation in solution and solid phase synthesis. The efficacy of the family of new N-triazinylammonium sulfonates as a coupling reagent in solution was examined using two models systems: Z-Aib-OH + H-Aib-OMe and Z-Leu-Phe-OH + H-Ile-OBu^t. The effectiveness of the family of N-triazinylammonium sulfonates in solid-phase mode was demonstrated in the synthesis of ACP(65-74) (ACP: H-Val-Gln-Ala-Ala-Ile-Asp-Tyr-Ile-Asn-Gly-OH), which is a good example of difficult peptide sequence, because of the development of internal secondary structures.

Acknowledgement: This work was supported by the Grant donated by the Technical University of Łódź.

[1] Kamiński, Z. J.; Kolesińska, B.; Kolesińska, J.; Jastrząbek, K. Eur. Pat. Appl. EP1586566 A1 from 19.10.2005, CA 143: 387385 (2006).
[2] Kolesińska, B.; Frączyk, J.; Papini, A.M.; Kamiński, Z.J., Chemistry Today (Chimica Oggi) 2007, 25(1), 26-29.

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