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Tuning the cis / trans Conformer Ratio of Xaa–Pro Amide Bonds by Intramolecular Hydrogen Bonds: The Effect on PPII Helix Stability
Author(s) -
Kuemin Michael,
Nagel Yvonne A.,
Schweizer Sabine,
Monnard Fabien W.,
Ochsenfeld Christian,
Wennemers Helma
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201001851
Subject(s) - conformational isomerism , intramolecular force , hydrogen bond , amide , chemistry , substituent , ring (chemistry) , polyproline helix , stereochemistry , helix (gastropod) , molecule , organic chemistry , peptide , ecology , biochemistry , snail , biology
The attraction of H‐bonding : Proline derivatives with a C4‐ endo ring pucker and a preference for the trans amide conformer are introduced as building blocks to tune the cis / trans amide conformer ratio in Xaa‐Pro bonds within peptides. Noncovalent interactions, such as hydrogen bonding between the substituent at C4 of the proline ring and the amide backbone are key for favoring or disfavoring the trans conformer (see picture).