Synthesis of addition polymers derived from enantiomerically pure amino acids

The synthesis of fully and partially protected serine derived monomers suitable for addition polymerization is reported, along with the homo- and copolymerization of these enantiomerically pure monomers. The monomers are all derived from (S)-serine methyl ester, by the introduction of an acryloyl or methacryloyl group onto the serine alcohol functionality. The fully protected monomers also contain a triphenylmethyl group on the serine amino group. The characterization of the resulting polymers using gel permeation chromatography, polarimetry, circular dichroism, elemental analysis and nuclear magnetic resonance is described. All of the polymers are atactic and optically active. The specific rotation of the polymers was found to vary in a non-linear manner with the proportion of chiral monomer incorporated into the polymers. (C) 1997 Elsevier Science Ltd.