One-step synthesis and regioselective polymerization of Nα,Nδ-bisphenoxycarbonyl-l-ornithine†
Abstract
N α,Nδ-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(Nδ-phenoxycarbonyl-L-ornithine). Three deprotection pathways quantitatively removing the Nδ-phenoxycarbonyl group, i.e., aminolysis, deprotection and guanidination, produce poly-L-citrulline, poly-L-ornithine and poly-L-arginine, respectively.