From prebiotic macromolecules to synthetic polypeptides: a new, efficient synthesis of α‐amino acid <i>N</i>‐carboxyanhydrides (NCAs)

Abstract

Abstract While polypeptide materials present important application potentialities, the expense of amino acid N ‐carboxyanhydride (NCA) monomers strongly limits their applications. We present here a new, promising synthetic route to NCA through N ‐carbamoylamino acid nitrosation by gaseous NO x (1 &lt; x &lt; 2) in the solid–gas phase. This very efficient reaction (which was originally developed in a prebiotic context) works in the absence of solvent and with minimum waste, and presents interesting economic features. Some mechanistic investigations aimed at the optimisation and scale‐up of this reaction in the solid‐gas phase are presented. © 2002 Society of Chemical Industry