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

Type
Label
  • Pseudopeptide foldamers. The homo-oligomers of benzyl (4S,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylate (Articolo in rivista) (literal)
Anno
  • 2003-01-01T00:00:00+01:00 (literal)
Alternative label
  • Tomasini C., Trigari V., Lucarini S., Bernardi F., Garavelli M., Peggion C., Formaggio F., Toniolo C. (2003)
    Pseudopeptide foldamers. The homo-oligomers of benzyl (4S,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylate
    in European journal of organic chemistry (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Tomasini C., Trigari V., Lucarini S., Bernardi F., Garavelli M., Peggion C., Formaggio F., Toniolo C. (literal)
Pagina inizio
  • 259 (literal)
Pagina fine
  • 267 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • - (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Titolo
  • Pseudopeptide foldamers. The homo-oligomers of benzyl (4S,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylate (literal)
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, 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. (literal)
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