Combining cyclic peptides with metal coordination

Abstract

This thesis targets cyclic peptide supramolecular structures for biomaterial applications. The introduction gives a brief insight into supramolecular interactions, peptides, and their application in biomaterials. These supramolecular interactions range from the weak forces of electrostatics and van der Waals interactions, to hydrogen bonding and metal-coordination. The application of peptides and supramolecular interactions has become a highly studied area of chemistry, which has quickly gotten attention in the area of biomaterials. The use of peptides in biomaterials seems obvious since in vivo rejection of this material might be limited. Nature can be used as a blue print to direct the path for hydrogen bonding motifs and metal-coordinating interactions and can be applied potentially towards supramolecular biomaterials. Finally, the introduction reviews the use of cyclic peptides and accounts for the synthetic design of the cyclic octapeptide to be used throughout the thesis work. The second chapter of the thesis provides the details by which the synthetic scheme for creating the linear peptides of interest and ultimately the cyclic peptides is described in detail. Many synthetic challenges were met and overcome during this thesis work; the most notable was overcoming purification challenges and poor amino acid coupling reactions that resulted in low yields. This thesis focuses primarily on the di-substituted pyridylalanine cyclic octapeptide, however much of the initial work on the mono-substituted cyclic octapepide was carried out in tandem allowing for comparison of the two peptides necessary for future work.