β-Pseudopeptide foldamers. the homo-oligomers of (4R)-(2-oxo-1,3-oxazolidin-4-yl)-acetic acid (D-Oxac)

Gianluigi Luppi, Roberta Galeazzi, Marco Garavelli, Fernando Formaggio, Claudia Tomasini

Research output: Contribution to journalArticlepeer-review

Abstract

A total synthesis in solution and a conformational analysis of the homo-oligomers of (4R)-(2-oxo-1,3-oxazolidin-4-yl)-acetic acid (D-Oxac) to the tetramer level are described. As the D-Oxac building block contains both an oxazolidin-2-one and a β-amino acid group, it may represent a new type of conformationally constrained tool for the construction of β-pseudopeptide foldamers. A conformational investigation using NMR and an extensive, unconstrained analysis with a Monte Carlo search to the octamer level, both in water and in chloroform, showed that these homo-oligomers tend to fold in a regular helical structure in a competitive solvent, such as water. Since aqueous solutions are of major relevance for biological systems, these molecules are good candidates for application to these environments.

Original languageEnglish
Pages (from-to)2181-2187
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume2
Issue number15
DOIs
Publication statusPublished - Aug 7 2004

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Chemistry(all)

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