Premium
Fructose‐Based Proline Analogues: Exploring the Prolyl trans / cis ‐Amide Rotamer Population in Model Peptides
Author(s) -
Cipolla Laura,
Airoldi Cristina,
Bini Davide,
Gregori Maria,
Marcelo Filipa,
JiménezBarbero Jesús,
Nicotra Francesco
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000983
Subject(s) - chemistry , proline , stereochemistry , conformational isomerism , moiety , amide , peptide , peptide bond , rational design , amino acid , molecule , biochemistry , organic chemistry , biology , genetics
A 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 experiments.