Density Functional Theory Studies on the Synthesis of Poly(α-Amino Acid)s Via the Amine-Mediated Ring Opening Polymerizations of N-Carboxyanhydrides and N-Thiocarboxyanhydrides

Tianwen Bai; Botuo Zheng; Jun Ling

doi:10.3389/fchem.2021.645949

Density Functional Theory Studies on the Synthesis of Poly(α-Amino Acid)s Via the Amine-Mediated Ring Opening Polymerizations of N-Carboxyanhydrides and N-Thiocarboxyanhydrides

Front Chem. 2021 Mar 29:9:645949. doi: 10.3389/fchem.2021.645949. eCollection 2021.

Authors

Tianwen Bai¹, Botuo Zheng¹, Jun Ling¹

Affiliation

¹ MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, China.

Abstract

To synthesize well-defined poly (α-amino acid)s (PAAs), ring opening polymerizations (ROP) of cyclic monomers of α-amino acid N-carboxyanhydrides (NCAs) and N-thiocarboxyanhydrides (NTAs) are most widely used. In this mini-review, we summarize the mechanism details of the monomer preparation and ROP. The present study used density functional theory calculations to reveal the mechanisms together with experimental phenomena in the past decades. Detailed discussion includes normal amine mechanism and the selectivity of the initiators bearing various nucleophilic groups.

Keywords: mechanism and kinetic; polymer synthesis; polypeptide; polypeptoid; quantum chemical calculation.

Publication types

Review