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Abstract

This paper describes the synthesis of several novel water- soluble highly branched polypeptides. The synthesis starts with the ring-opening polymerization of ε-benzyloxycarbonyl-L-lysine N-carboxyanhydride (Z-Lys NCA) or ε-trifluoroacetyl-L-lysine N-carboxyanhydride (TFA-Lys NCA), followed by end functionalization of the peptide chain with N^α,N^ε-di(9-fluorenylmethoxycarbonyl)-L-lysine (N^α,N^ε-diFmoc Lys). Deprotection of the N^α,N^ε-diFmoc Lys end group affords two new primary amine groups that can initiate the polymerization of a second generation of branches. Repetition of this ring-opening polymerization-end functionalization sequence affords highly branched poly(ε-benzyloxycarbonyl-L-lysine) (poly(Z-Lys)) and poly(ε-trifluoroacetyl-L-lysine) (poly(TFA-Lys)) in a small number of straightforward synthetic steps. Removal of the side-chain protective groups yields water-soluble and highly branched poly(L-lysine)s, which may be of potential interest for a variety of medical applications.