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 |
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| Authors: | Arianna Greco Sara Tani Rossella De?Marco Luca Gentilucci |
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| Affiliation: | Dept. of Chemistry “G. Ciamician”, University of Bologna via Selmi 2, 40126, Bologna (Italy), Fax: (+39)?0512099456 |
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| 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‐β2‐ or α‐substituted‐α‐hydroxy‐β2, 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 β2, 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. |
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| Keywords: | chain structures conformation analysis Freidinger lactams peptidomimetics amino acids |
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