Large structural modification with conserved conformation: analysis of delta(3)-fused aryl prolines in model beta-turns.
For the first time, the influence of a fused Delta3-arylproline on peptide conformation has been studied by the synthesis and comparison of the conformations of peptides containing proline and pyrrolo-proline, 3 (PyPro). Pyrrolo-proline was demonstrated to be a conservative replacement for Pro in model beta-turns, 4 and 5, as shown by their similar DMSO titration curves, cis/trans-isomer populations, and NOESY spectral data. Pyrrolo-proline may thus be used for studying the structure activity relationships of Pro-containing peptides with minimal modification of secondary structures.
Jeannotte
Guillaume
G
Département de chimie, Université de Montréal, C.P. 6128, Succursale CentreVille, Montréal, Québec, Canada H3C 3J7.
Lubell
William D
WD
D019906:Nuclear Magnetic Resonance, Biomolecular; D009842:Oligopeptides / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D011487:Protein Conformation; D017433:Protein Structure, Secondary
D009842:Oligopeptides; D011392:Proline