ABSTRACT:We report methods for the synthesis of polypeptides that are fully functionalized with desirable phosphorylcholine, PC, groups. Due to inherent challenges in the direct incorporation of the PC group into α-amino acid N-carboxyanhydride (NCA) monomers, we developed a synthetic approach that combined functional NCA polymerization with efficient postpolymerization modification. While poly(L-phosphorylcholine serine) was found to be unstable upon synthesis, we successfully prepared poly(L-phosphorylcholine homoserine) with controlled chain lengths, and found these to be water soluble with disordered chain conformations.