Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 41, Pages 13390-13404Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201402519
Keywords
chain structures; conformation analysis; Freidinger lactams; peptidomimetics; amino acids
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Funding
- Fondazione Umberto Veronesi, Milano/Roma, MIUR (PRIN)
- Italian Minister for Foreign Affairs
- Fondazione per la Ricerca sulla Fibrosi Cistica, Verona [FFC#11/2011]
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Constrained peptidomimetic scaffolds are of considerable interest for the design of therapeutically useful analogues of bioactive peptides. We present the single-step cyclization of (S)- or (R)-alpha-hydroxy-I32- or alpha-substituted-alpha-hyd roxy-I32'2-amino acids already incorporated within oligopeptides to 5-aminomethyl-oxazolidine-2,4-dione (Amo) rings. These scaffolds can be regarded as unprecedented 132- or 132'2-homo-Freidinger lactam analogues, and can be equipped with a proteinogenic side chain at each residue. In a biomimetic environment, Amo rings act as inducers of extended, semi-bent or folded geometries, depending on the relative stereochemistry and the presence of alpha-substituents.
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