Two types of glucose-responsive copolymers poly(lactide)-block- poly(dimethylamino-2-ethyl methacrylate)-block-polyvinyl phenylboronic acid (PLA-b-PDMAEMA-b-PVBA) and poly(lactide)-block-(poly(dimethylamino-2-ethyl methacrylate)-co-polyvinyl phenylboronic acid) [PLA-b-(PDMAEMA-co-PVBA)] were synthesized by one-step and two-step Reversible Addition-Fragmentation Chain Transfer Polymerization (RAFT), respectively, via polylactic acid (PLA) macromolecular as a chain transfer agent. These chemical structures of the copolymers had been controlled. Assembly behavior studies indicate that PLA-b-(PDMAEMA-co-PVBA) could self-assemble to form micelles in selective solvents, while PLA-b-(PDMAEMA-b-PVBA) could form micelles in glucose solvent only. Both micelles showed a good glucose-responsive property, and their particle size and morphology changed with the variation of glucose concentration.