Fructose-Based Proline Analogues: Exploring the Prolyl trans/cis-Amide Rotamer Population in Model Peptides

9 páginas, 4 figuras, 2 tablas, 2 esquemas -- PAGS nros. 128-136A D-fructose moiety in which a D-proline ring has been engineered with a spiranic junction in the glycidic scaffold has been used as a proline mimetic. The bicyclic structure, which possesses high structural rigidity, was then included in model peptides to explore their prolyl cis/trans amide rotamer populations. Model peptide conformations were studied by molecular dynamics and NMR experimentsWe gratefully acknowledge financial support by Regione Lombardia (Programma Operativo Regione Lombardia Ob. 3 Fondo Sociale Europeo 2000–2006), Sovvenzione Globale Progetto Ingenio A0001127/2007, Consorzio Interuniversitario Nazionale “Metodologie e Processi Innovativi di Sintesi” (C.I.N.M.P.I.S.) and the Fondo di Ateneo per la Ricerca FAR 2008. The Fundação para Ciência e Tecnologia (FCT) Portugal is also thanked for post-doctoral research (grant SFRH/BDP/65462/2009)Peer reviewe