Oxidative Coupling of phenol-containing precursor poly(amino acid)s, poly(alpha-glutamine), poly(alpha/beta-asparagine), and poly(gamma-glutamine) derivatives, has been examined to produce a new class of soluble poly(amino acid)s. Under appropriate reaction conditions, the Fe-salen and HRP catalysts efficiently induced the oxidative coupling without formation of insoluble gels, yielding the soluble polymers of high molecular weight. The oxidative coupling behaviors were greatly influenced by the structure: and phenol content of the precursor polymer. The selection of the substrate concentration and catalyst amount was crucial for the production of soluble polymers of high molecular weight.