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

An alternative method for the synthesis of pseudopeptides containing a w[CH2NH] amide bond surrogate is reported. The synthetic approach is based on a nucleophilic displacement of the chiral N-protected b-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 w[CH2NH] peptide bond isostere in peptide chemistry