Biocompatible and proteolysis-resistant β-amino acid polymers, containing poly-β-peptide, poly-α/β-peptide and poly-β-peptoid, exert important biological functions in the research fields of peptide mimics, biomimetic polymer and antibacterial. However, the functional study and application of β-amino acid polymers were greatly hindered by the harsh and water-sensitive polymerization condition, the limited structural diversity and difficult in sequence-control. Herein, we firstly develop a water-insensitive and controllable ring-opening polymerization of β-amino acid N-thiocarboxyanhydrides (β-NTAs) that can be operated in open vessels to prepare poly-β-peptides in high yields, with diverse functional groups, variable chain length, narrow dispersity and defined architecture. Secondly, we report the copolymerization on α-amino acid N-carboxyanhydrides (α-NCA) and β-NTA for sequence-controlled synthesis of poly-α/β-peptide. This copolymerization strategy present solvent-tuning polymerization characteristics, which provides random-like copolymers of poly-α/β-peptides in THF and block-like copolymers of poly-α/β-peptides in a mixed solvent of CH3Cl/H2O (95/5, v/v). In addition, β-NTA polymerization inspire us to prepare poly-β-peptoids via the polymerization on N-substituted β-NTA monomers (β-NNTAs), we demonstrated a controllable β-NNTA polymerization for convenient synthesis of poly(β-peptoid)s bearing diverse functionalities using variable primary amine as initiators. Our studies highlight the superior advantages of β-NTA polymerization chemistry for various β-amino acid polymers synthesis, functional study and application as synthetic mimics of peptides.

Water-insensitive and controllable synthesis of β-amino acid polymers via polymerization on β-amino acid N-thiocarboxyanhydrides

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