Solid phase synthesis of Ψ[CH(CN)NH] pseudopeptides. Application to the synthesis of analogues of neurotensin [NT(8-13)]

The introduction of the cyanomethyleneamino [CH(CN)NH] group, a new type of peptide bond surrogate, under solid phase peptide synthesis conditions has been studied using both Boc and Fmoc strategies. The pseudohexapeptides H-Arg-Pro-Tyrψ[CH(CN)NH]Ile-Leu-OH (1) and H-Arg-Arg-Pro-Tyr-Ileψ[CH(CN)NH]Leu-OH (2), analogues of the C-terminal hexapeptide of neurotensin [NT(8–13)], were successfully obtained via Fmoc synthesis. The solid phase synthesis of the ψ[CH(CN)NH] pseudopeptides 1 and 2, NT(8–13) analogues, is described.We thank Novo Nordisk A/S, Comisión Interministerial de Ciencia y Tecnología and Cornunidad Autónoma de Madrid for financial support