Alternating Asymmetric Self-induction in Functionalized Pyrrolidine Oligomers

摘要

Artificial structurally well-defined polymers have excited interest as functional mimetics of natural biomacromolecules, exhibiting additional properties not occurring in the living world. Specific conformational organization of natural and synthetic polymeric objects leading to unique folding accounts for the molecular recognition, which is one of the driving principles in important natural processes. Some non-natural oligomeric species adopt specific and well-defined conformations dictated by the structure of monomeric units and intramolecular interactions and are defined as foldam-ers. One of the most studied unnatural foldamer types are β-peptides that adopt stable folded helical, sheet, and turn-like conformations. β-Peptides are stable towards natural enzymes, and appropriate design leads to discovery of (3-peptide ligands for complicated pharmaceutical targets, such as protein-protein interactions. The application of pyrroli-dine-3-carboxyiic acid (Pca) for the construction of β-polypeptide chain rigidities the molecular backbone and provides additional stabilization of the secondary structure of the oligomer in solution.