Pseudopeptide foldamers. The homo-oligomers of benzyl (4S,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylate

A 2-oxo-1,3-oxazolidine-4-carboxylic acid was designed as a new, conformationally restricted building block for the construction of pseudopeptide foldamers. IR, H-1 NMR and CD techniques, implemented by detailed DFT computational modeling, were exploited to investigate the preferred three-dimensional structure of benzyl (4S,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylate homo-oligomers synthesized to the pentamer level. The resulting poly(L-Pro), 11 like helical conformation was found to be stabilized by intramolecular alphaC-H...O=C hydrogen bonds. This novel, acylurethane-based, ternary foldameric structure, if appropriately functionalized, holds promise as a robust template for a variety of applications.