One-step synthesis and regioselective polymerization of Nα,Nδ-bisphenoxycarbonyl-l-ornithine

Abstract

N _α,N_δ-Bisphenoxycarbonyl-L-ornithine is synthesized by a one-step protection of L-ornithine, and it acts as a monomer for regioselective and controlled polymerization to yield poly(N_δ-phenoxycarbonyl-L-ornithine). Three deprotection pathways quantitatively removing the N_δ-phenoxycarbonyl group, i.e., aminolysis, deprotection and guanidination, produce poly-L-citrulline, poly-L-ornithine and poly-L-arginine, respectively.