Azatides: Solution and Liquid Phase Syntheses of a New Peptidomimetic

Abstract

An efficient method has been developed for the solution and liquid phase syntheses of a biopolymer mimetic consisting of “α-aza-amino acids” linked in a repetitive manner to form what we term an azatide oligomer. To construct this biopolymer mimetic, three stages of research were pursued as follows: (1) development of general synthetic procedures that allowed the synthesis of a wide variety of Boc-protected aza-amino acid monomers, (2) optimization of solution phase procedures for the coupling of aza-amino acids in a repetitive manner, and (3) design and synthesis of a linker that would support azatide synthesis using a liquid phase synthetic format. The successful completion of these three phases of research demonstrates that oligoazatides can now be rapidly assembled on a homogeneous polymeric support. The long term prospectus of this new biopolymer is the exploration of peptide structure as well as a potential source of new peptidomimetic libraries.