Α-Amino acid N-thiocarboxyanhydrides: A novel synthetic approach toward poly(α-amino acid)s. (December 2018)

• Record Type: Journal Article
• Authors: Tao, Xinfeng; Li, Min-Hui; Ling, Jun
• Is Part Of: European polymer journal. Volume 109(2018)
• Page Start: 26
• Page End: 42
• Publication Date: 2018-12
• Subjects: Polypeptides -- Polypeptoids -- Ring opening polymerization -- N-thiocarboxyanhydrides -- Sarcosine; Polymers -- Periodicals; Polymerization -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; Polymerization; Polymers; Periodicals; Electronic journals; 547.705
• DOI: 10.1016/j.eurpolymj.2018.08.039
• Languages: English
• ISSNs: 0014-3057

Abstract

Graphical abstract: Abstract: Poly(α-amino acid)s, containing amino acid repeat units, are remarkable biomaterials with similar structures to protein, which are mainly synthesized by solid phase peptide synthesis, ring opening polymerization of N -carboxyanhydrides, polymerization of activated urethane derivatives of α-amino acids and so on. α-Amino acid N -thiocarboxyanhydride (NTA) and N -substituted glycine N -thiocarboxyanhydride (NNTA) have recently emerged as a subject of scientific interest due to their easy synthesis and purification in open air, long shelf-life and well controlled polymerization to produce poly(α-amino acid)s. In this feature article, we review the history and the recent development on the design of NTA monomers, and summarize the recent advances in poly(α-amino acid)s synthesis through ring-opening polymerization of NTA and NNTA by using different initiators and reaction mediums. We also highlight the applications of poly(α-amino acid) materials resulting from NTA polymerization.