Synthesis of (3R)-carboxy pyrrolidine (a beta-proline analogue) and its oligomer

Abstract

A decamer of a beta-amino acid analogue of L-proline, (3R)-carboxy pyrrolidine (beta-proline), was synthesized from a readily available (R)-glycidol. It was found to possess a rigid secondary structure, as evidenced by its CD spectrum. The beta-proline decamer, however, failed to bind to profilin, whereas the corresponding alpha-L-proline decamer bound tightly to this protein.