Progress toward the synthesis of arginine-glycine-aspartic acid (R-G-D) analogues and asymmetric atom transfer reactions

Progress toward new moieties that feature the arginine-glycine-aspartic acid (RGD) motif were examined. Two sets of RGD analogues were investigated. One set is a cyclic peptide derivative and the other set is new RGD-based biomaterials that take advantage of modern polymerization techniques such as ring opening metathesis polymerization (ROMP) and acyclic diene metathesis (ADMET). Other investigations discussed here include asymmetric atom transfer reactions and polymer supported Diels-Alder reactions.; RGD is a tripeptide recognition sequence that is composed of three amino acids: arginine, glycine, and aspartic acid. This sequence is recognized by receptors on the extracellular matrix that in turn are responsible for the adhesive properties of cells. The synthesis of a new proline-based RGD analogue was undertaken and completed using traditional solid phase technique. With this analogue in hand biological testing is the next step.; A second RGD analogue has been investigated for potential for use as a new biomaterial. With an azabicyclic scaffold, investigations into ROMP and ADMET materials were attempted with model studies focused on synthesis of materials that can be incorporated in solid phase synthesis. Progress towards substrates for incorporation into the methodology were investigated.; Asymmetric atom transfer reactions under the influence of a carbohydrate scaffold were also investigated. Atom transfer processes were investigated under a number of conditions to find optimal conditions for stereochemical transfer. With variation in temperature, solvent, and Lewis acid a potentially useful synthetic process has been shown.; Finally, soluble polymer systems were made to study the Diels-Alder reaction. With the design of soluble polymer systems, clean products with lack of purification should result. In this study a Diels alder reaction with the use of soluble polymer supports was investigated in the presence carbohydrate chiral auxiliary.