Intramolecular amide stacking and its competition with hydrogen bonding in a small foldamer.
J Am Chem Soc
; 131(40): 14243-5, 2009 Oct 14.
Article
in En
| MEDLINE
| ID: mdl-19757786
ABSTRACT
Attractive interactions between two carboxamide groups in a "stacked" geometry are explored under isolated molecule conditions. Infrared spectra of single conformations of a small gamma-peptide, Ac-gamma(2)-hPhe-NHMe, reveal the presence of a conformation in which the two amide planes are approximately parallel with the amide dipoles in an antialigned orientation. This stacked conformation is energetically comparable to conformations that contain an intramolecular amide-amide H-bond. Amide stacking interactions can compete with H-bonding in circumstances where the amide groups can be brought into a stacking configuration with minimal strain, opening the way for its use in the design of future foldamer structures.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Peptides
/
Amides
Language:
En
Journal:
J Am Chem Soc
Year:
2009
Document type:
Article
Affiliation country:
United States