Nonpeptidic Reverse Turn that Promotes Parallel Sheet Structure Stabilized by C----H···O Hydrogen Bonds in a Cyclopropane γ-Peptide

Nonpeptidic Reverse Turn that Promotes Parallel Sheet Structure Stabilized by C----H···O Hydrogen Bonds in a Cyclopropane γ-Peptide

A twist of fate: Parallel‐turn linkers comprising an amino acid derived alcohol conjoined with an aromatic amide through a flexible linkage adopt reverse‐turn conformations. Cyclopropane tetra‐ and hexapeptide analogues form a CH⋅⋅⋅O hydrogen‐bond‐stabilized parallel‐sheet conformation (see scheme)...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2008-09, Vol.47 (37), p.7099-7102
Hauptverfasser: Jones, Christopher R, Qureshi, M. Khurram N, Truscott, Fiona R, Hsu, Shang-Te Danny, Morrison, Angus J, Smith, Martin D
Format: Artikel
Sprache:eng
Schlagworte:
foldamers
hydrogen bonds
parallel turns
peptidomimetics
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Beschreibung
Zusammenfassung:A twist of fate: Parallel‐turn linkers comprising an amino acid derived alcohol conjoined with an aromatic amide through a flexible linkage adopt reverse‐turn conformations. Cyclopropane tetra‐ and hexapeptide analogues form a CH⋅⋅⋅O hydrogen‐bond‐stabilized parallel‐sheet conformation (see scheme). NMR studies confirm the presence of hydrogen bonds in these structures.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200802648