Dynamic amino acid functional materials

Abstract

Amino acid functional materials show promise in many biological applications. The responsive properties of amino acid R-groups, such as metal ion coordination and pH response, have been used in the design of new biologically inspired materials. However, the synthesis of amino acid functional materials is often tedious and difficult, requiring multiple protection steps. Especially, the synthesis of histidine functional materials has been problematic in the literature due to the reactive imidazole group. Here, reductive amination is used as a versatile synthetic method for the synthesis of amino acid functional materials without protecting groups. The synthesis of histidine functional polymers is highlighted. Dynamic imine chemistry is explored to change the amino acid functionality of the polymer. Reductive amination is used to functionalise block copolymers with histidine and metal ion coordination is used to stabilise the micelles. Finally, carbonyl condensation chemistry is used to synthesise self-healing gels form aldehyde functional polymers, where amino acid functionality is easily added.