The first (PG1) and second (PG2) generation dendronized polymethacrylates with L-lySine based dendrons have been synthesized, and their conformation has been investigated. The chiral dendrons can be synthesized efficiently on a multi-gram scale from L-lySine by a solution peptide coupling method, and the over-all yields for the first (MG1) and second (MG2) generation macromonomers are 77 and 75%, respectively. High molar masses (1 to 2 million) of PG1 and PG2 are achieved by conventional radical polymerization of the corresponding macromonomers. Characterization with optical rotation, circular dichroism, and UV measurements showed that, in contrast to PG1, PG2 adopts a single-handed helical conformation in solution, which is stable in different polar solvents and also over a broad temperature range. Interestingly, the stable helical conformation remained in aqueous solution after deprotection of the terminal amines, by which the mass and steric hindrance of the dendrons reduced significantly.