Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 22, Pages 5552-5566Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200802078
Keywords
ab initio calculations; amino acids; foldamers; mixed helices; peptides
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Funding
- CSIR, New Delhi
- Deutsche Forschungsgemeinschaft [HO-2346/1-3, 610]
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Stimulated by an overview on all periodic folding patterns of alpha/delta-hybrid peptides with 1:1 alternating backbone provided by ab initio molecular orbital theory, the first representatives of this foldamer class were synthesized connecting novel C-linked carbo-delta-amino acid constituents and L-Ala. In agreement with theoretical predictions, extensive NMR spectroscopic analyses confirm the formation of new motifs of 13/11-mixed helical patterns in these peptides supported by the rigidity of the D-xylose side chain in the selected delta-amino acid constituents. Relationships between possible helix types in alpha/delta-hybrid peptides and their counterparts in other 1:1 hybrid peptide classes and native alpha-peptides are discussed these indicate the high potential of these foldamers to mimic native peptide secondary structures. The design of alpha/delta-hybrid peptides provides ail opportunity to expand the domain of foldamers and allows the introduction of desired functionalities through the alpha-amino acid constituents.
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