Tuning the cis/trans Conformer Ratio of Xaa-Pro Amide Bonds by Intramolecular Hydrogen Bonds: The Effect on PPII Helix Stability

Tuning the cis/trans Conformer Ratio of Xaa-Pro Amide Bonds by Intramolecular Hydrogen Bonds: The Effect on PPII Helix Stability

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 su...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2010-08, Vol.49 (36), p.6324-6327
Hauptverfasser: Kuemin, Michael, Nagel, Yvonne A, Schweizer, Sabine, Monnard, Fabien W, Ochsenfeld, Christian, Wennemers, Helma
Format: Artikel
Sprache:eng
Schlagworte:
ab initio calculations
Amides - chemistry
conformation analysis
Dipeptides - chemistry
helical structures
Hydrogen Bonding
Isomerism
isomerization
peptides
Proline - chemistry
Protein Structure, Secondary
Thermodynamics
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Beschreibung
Zusammenfassung: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).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201001851