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, 1H 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)n II like helical conformation was found to be stabilized by intramolecular α-C−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.
Pseudopeptide Foldamers − The Homo-Oligomers of Benzyl (4S,5R)-5-Methyl-2-oxo-1,3-oxazolidine-4-carboxylate
LUCARINI, SIMONE;
2003
Abstract
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, 1H 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)n II like helical conformation was found to be stabilized by intramolecular α-C−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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
