There is great current interest in the design of robust synthetic polymers for the preparation of novel functional, well-defined, biocompatible and tailorable materials for a range of possible applications. In this work we have used reversible addition fragmentation chain transfer (RAFT) polymerization to prepare chiral and responsive amphiphilic block copolymers (based on polyphenylalanine acrylamide), which can be assembled at different pHs to form well-defined nanostructures. The morphology and size of the derived block polymers were explored using TEM, DLS and SLS measurements, while stability was examined by fluorescence and NMR spectroscopy. The application of these chiral and responsive nanostructures in the resolution of hydrophilic racemic amino acids has also been explored.