We use reversible addition-fragmentation chain transfer (RAFT) polymerization of amino acid based vinyl monomers to prepare macromolecular materials with well-defined architecture, controlled molecular weight, narrow molecular weight distribution and precise end-functionalities. These chiral polymers show smart pH-responsiveness and cationic character in aqueous media. Also, these side-chain containing amino acid based polymers show low cytotoxicity, which facilitate consideration of these materials for several applications such as, drug/gene delivery, catalysis, chiral recognition, etc.