Copolymerization of peptide derived monomers and methyl methacrylate

The copolymerization of a series of peptide derived (meth)acrylate derivatives with methyl methacrylate is reported. The resulting polymers are optically active and display a variety of non-linear dependencies of specific rotation against %-chiral monomer incorporation. The polymers contain acid labile protecting groups that can be removed to generate a second series of polymers, which also show non-linear dependencies of specific rotation against %-chiral monomer incorporation. All of the non-linear effects can be explained by a model based on asymmetric induction from the stereocenters within the peptide, to prochiral centers within the peptide unit and the adjacent methyl methacrylate unit.