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Polypeptoids bearing carboxylic acid groups on the N -substituent are useful building blocks for the construction of peptidomimetic supramolecular assemblies with stimuli-responsive properties. Towards this end, N -(3- tert -butoxy-3-oxopropyl) glycine derived N -carboxyanhydride ( t BuO 2 Pr-NCA) has been successfully synthesized and polymerized using primary amine initiators to produce the corresponding poly( N -(3- tert -butoxy-3-oxopropyl) glycine) with molecular weights ( M n ) of 5.6–59 kg mol −1 and a narrow molecular weight distribution (PDI = 1.003–1.026). The polymerization was shown to proceed in a controlled manner, evidenced by the good agreement of the experimental molecular weight ( M n ) with theoretical values and narrow molecular weight distribution in a wide range of monomer-to-initiator ratios ([M] 0  : [I] 0 = 25 : 1–200 : 1), the linear increase of M n with conversion and the second-order polymerization kinetics. The cloaked carboxyl groups on the poly( N -(3- tert -butoxy-3-oxopropyl) glycine) can be readily unveiled in mild acidic conditions to yield the poly( N -(2-carboxyethyl) glycine), a structural mimic of poly(glutamic acid). The poly( N -(2-carboxyethyl) glycine) polymer is a weak polyelectrolyte whose hydrodynamic size in water can be controlled by the solution pH. 

Polypeptoids, a class of peptidomimetic polymers, have emerged at the forefront of macromolecular and supramolecular science and engineering as the technological relevance of these polymers continues to be demonstrated. The chemical and structural diversity of polypeptoids have enabled access to and adjustment of a variety of physicochemical and biological properties (eg, solubility, charge characteristics, chain conformation, HLB, thermal processability, degradability, cytotoxicity and immunogenicity). These attributes have made this synthetic polymer platform a potential candidate for various biomedical and biotechnological applications. This review will provide an overview of recent development in synthetic methods to access polypeptoid polymers with well‐defined structures and highlight some of the fundamental physicochemical and biological properties of polypeptoids that are pertinent to the future development of functional materials based on polypeptoids.