From Polyesters to Polyamides Via ON Acyl Migration: An Original Multi-Transfer Reaction

Julien Tailhades (1) , Sébastien Blanquer (1) , Benjamin Nottelet (1) , Jean Coudane (1) , Gilles Subra (1) , Pascal Verdié (1) , Etienne Schacht (2) , Jean Martínez (1) , Muriel Amblard (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]
2 UGENT - Universiteit Gent = Ghent University

A new strategy for the synthesis of polyamides from polyesters of hydroxyl‐containing amino acids using a multi ON acyl transfer reaction was developed. This original approach allowed the synthesis of three generations of polymers from the same starting monomer. The polymerization of N‐benzyloxycarbonyl‐serine and its γ‐homologated derivative provided the Z‐protected polyesters; then the water‐soluble polycationic polyesters were obtained by removal of the Z‐protecting group; and finally the polyamides were obtained by a base‐induced multi ON acyl transfer, both in aqueous or organic medium. The key step transfer reaction was monitored by the disappearance and appearance of characteristic NMR proton signals and IR bands of polyesters and polyamides.

Mots clés: multi O-N acyl migration; Polycationic polyester; Polypeptide amide; Polypeptide ester; Switchable biopolymer

Domaines: Chimie; Polymères

Julien Tailhades, Sébastien Blanquer, Benjamin Nottelet, Jean Coudane, Gilles Subra, et al.. From Polyesters to Polyamides Via ON Acyl Migration: An Original Multi-Transfer Reaction. Macromolecular Rapid Communications, 2011, 32 (12), pp.876 - 880. ⟨10.1002/marc.201100235⟩. ⟨hal-01833151⟩