Synthesis and Analysis of the Conformational Preferences of 5‐Aminomethyloxazolidine‐2, 4‐dione Scaffolds: First Examples of β2‐ and β2,  2‐Homo‐Freidinger Lactam Analogues. Issue 41 (2nd September 2014)

• Record Type: Journal Article
• Authors: Greco, Arianna; Tani, Sara; De Marco, Rossella; Gentilucci, Luca
• Is Part Of: Chemistry. Volume 20:Issue 41(2014)
• Page Start: 13390
• Page End: 13404
• Publication Date: 2014-09-02
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201402519
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Constrained peptidomimetic scaffolds are of considerable interest for the design of therapeutically useful analogues of bioactive peptides. We present the single‐step cyclization of (<italic>S</italic>)‐ or (<italic>R</italic>)‐α‐hydroxy‐β²‐ 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 β²‐ 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.</p> </abstract>