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Pseudopeptide Foldamers − The Homo‐Oligomers of Benzyl (4 S ,5 R )‐5‐Methyl‐2‐oxo‐1,3‐oxazolidine‐4‐carboxylate
Author(s) -
Tomasini Claudia,
Trigari Valerio,
Lucarini Simone,
Bernardi Fernando,
Garavelli Marco,
Peggion Cristina,
Formaggio Fernando,
Toniolo Claudio
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200390027
Subject(s) - chemistry , oxazolidine , pentamer , intramolecular force , hydrogen bond , carboxylate , stereochemistry , conformational isomerism , cyclopentadiene , crystallography , molecule , organic chemistry , catalysis , biochemistry
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, 1 H NMR and CD techniques, implemented by detailed DFT computational modeling, were exploited to investigate the preferred three‐dimensional structure of benzyl (4 S ,5 R )‐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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)