Novel route in the synthesis of ψ[CH2NH] amide bond surrogate

Abstract An alternative method for the synthesis of pseudopeptides containing a ψ [CH 2 NH] amide bond surrogate is reported. The synthetic approach is based on a nucleophilic displacement of the chiral N-protected β-iodoamines with conveniently protected amino acid esters. The compatibility of this method with both conventional and microwave-assisted peptide synthesis should increase the potentiality of the ψ [CH 2 NH] peptide bond isostere in peptide chemistry.