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From prebiotic macromolecules to synthetic polypeptides: a new, efficient synthesis of α‐amino acid N ‐carboxyanhydrides (NCAs)
Author(s) -
Boiteau Laurent,
Collet Hélène,
Lagrille Olivier,
Taillades Jacques,
Vayaboury Willy,
Giani Olivia,
Schué François,
Commeyras Auguste
Publication year - 2002
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.946
Subject(s) - context (archaeology) , prebiotic , chemistry , macromolecule , amino acid , monomer , gas phase , nitrosation , organic chemistry , combinatorial chemistry , polymer , biochemistry , biology , paleontology
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 < x < 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