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Pseudopeptide Foldamers − The Homo-Oligomers of Benzyl (4S,5R)-5-Methyl-2-oxo-1,3-oxazolidine-4-carboxylate

✍ Scribed by Claudia Tomasini; Valerio Trigari; Simone Lucarini; Fernando Bernardi; Marco Garavelli; Cristina Peggion; Fernando Formaggio; Claudio Toniolo

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
620 KB
Volume
2003
Category
Article
ISSN
1434-193X

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✦ Synopsis

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, ^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)

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