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. The prolyl cis/trans amide rotamer populations of model peptides containing a proline mimetic constructed from a D-fructose scaffold have been explored. A conformational analysis was performed by molecular dynamics and NMR studies. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Cipolla, L., Airoldi, C., Bini, D., Gregori, M., Marcelo, F., Jiménez Barbero, J., et al. (2011). Fructose-Based Proline Analogues: Exploring the Prolyl trans/cis-Amide Rotamer Population in Model Peptides. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011(1), 128-136 [10.1002/ejoc.201000983].
Fructose-Based Proline Analogues: Exploring the Prolyl trans/cis-Amide Rotamer Population in Model Peptides
CIPOLLA, LAURA FRANCESCA;AIROLDI, CRISTINA;BINI, DAVIDE;GREGORI, MARIA;NICOTRA, FRANCESCO
2011
Abstract
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. The prolyl cis/trans amide rotamer populations of model peptides containing a proline mimetic constructed from a D-fructose scaffold have been explored. A conformational analysis was performed by molecular dynamics and NMR studies. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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