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)-α-hydroxy-β(2)- or α-substituted-α-hydroxy-β(2, 2)-amino acids already incorporated within oligopeptides to 5-aminomethyl-oxazolidine-2,4-dione (Amo) rings. These scaffolds can be regarded as unprecedented β(2)- or β(2, 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 α-substituents.
Synthesis and Analysis of the Conformational Preferences of 5- Aminomethyloxazolidine-2,4-dione Scaffolds: First Examples of beta2- and beta2,2-Homo-Freidinger Lactam Analogues / Arianna Greco; Sara Tani; Rossella De Marco; Luca Gentilucci. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - STAMPA. - 20:41(2014), pp. 13390-13404. [10.1002/chem.201402519]
Synthesis and Analysis of the Conformational Preferences of 5- Aminomethyloxazolidine-2,4-dione Scaffolds: First Examples of beta2- and beta2,2-Homo-Freidinger Lactam Analogues
GRECO, ARIANNA;TANI, SARA;DE MARCO, ROSSELLA;GENTILUCCI, LUCA
2014
Abstract
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)-α-hydroxy-β(2)- or α-substituted-α-hydroxy-β(2, 2)-amino acids already incorporated within oligopeptides to 5-aminomethyl-oxazolidine-2,4-dione (Amo) rings. These scaffolds can be regarded as unprecedented β(2)- or β(2, 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 α-substituents.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.