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.
Novel route in the synthesis of [CH2NH] amide bond surrogate / P., Campiglia; C., Aquino; A., Bertamino; M., Sala; GOMEZ MONTERREY, ISABEL MARIA; Novellino, Ettore; Grieco, Paolo. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - ELETTRONICO. - 49:(2008), pp. 731-734. [10.1016/j.tetlet.2007.11.112]
Novel route in the synthesis of [CH2NH] amide bond surrogate
GOMEZ MONTERREY, ISABEL MARIA;NOVELLINO, ETTORE;GRIECO, PAOLO
2008
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
