Temperature- and pH-sensitive homopolymer having chiroptical property was synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization of a threonine-containing acrylamide, N-acryloyl-L-threonine (A-(L)Thr-OH), followed by methylation. The LCST-type thermoresponsive property of poly(A-(L)Thr-OMe) was observed in aqueous solutions, and the transition temperature could be changed remarkably by pH value. The addition of urea also led to the increase in the transition temperature, suggesting that the hydrogen-bonding is a crucial factor to manipulate the thermoresponsive properties. Well-defined polymers having different chirality and hydrophilicity, poly(A-(D)Thr-OMe) and poly(A-(L)Ser-OMe), were also prepared from N-acryloyl-D-threonine (A-(D)Thr-OH) and N-acryloyl-L-serine (A-(L)Ser-OH). We evaluated the effects of pH, urea, and salt in aqueous solutions, and hydrophobicity, chirality, and molecular weights of the resulting polymers on the dual stimuli-responsive and chiroptical properties. (C) 2016 Elsevier Ltd. All rights reserved.