Conformational Analysis of Azabicycloalkane Amino Acid Scaffolds as Reverse-Turn Inducer Dipeptide Mimics

✍ Scribed by Laura Belvisi; Anna Bernardi; Leonardo Manzoni; Donatella Potenza; Carlo Scolastico

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 312 KB
• Volume: 2000
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/1099-0690(200007)2000:14<2563::aid-ejoc2563>3.0.co;2-3

✦ Synopsis

In an effort to design structural mimics of protein and peptide reverse-turns, the conformations of 5,5-, 6,5-, and 7,5-fused 1-aza-2-oxobicycloalkane amino acids have been evaluated. The conformational preferences of these proline-derived bicyclic lactams have been studied by Monte Carlo molecular mechanics searches, and the reverse-turn inducing properties of the calculated structures have been quantitatively assessed using various geometrical parameters. All of the four possible diastereoisomers arising from two of the three stereogenic centres [C3 and bridgehead carbon atom; Pro Cα is (S) in all compounds] have been considered for each bicyclic