A new spirocyclic proline-based lactam as efficient type II′ β-turn inducing peptidomimetic

✍ Scribed by Giordano Lesma; Alessia Colombo; Alessandro Sacchetti; Alessandra Silvani

• Book ID: 104095949
• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 215 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.10.072

✦ Synopsis

A new proline-based spirotricyclic lactam is reported as an efficient type II 0 b-turn inducing peptidomimetic. After investigations of the reverse turn properties by computational techniques, the scaffold has been synthesized by a straightforward sequence relying on a key RCM reaction for the construction of the spirocyclic lactams ring. For its conformational properties, the scaffold can be considered a privileged structure to be employed as a mimic of the b-turn motif of the potent antibiotic Gramicidin S.