Helix formation in preorganized beta/gamma-peptide foldamers: hydrogen-bond analogy to the alpha-helix without alpha-amino acid residues

J Am Chem Soc. 2010 Jun 16;132(23):7868-9. doi: 10.1021/ja103233a.

Abstract

We report the first high-resolution structural data for the beta/gamma-peptide 13-helix (i,i+3 C=O...H-N H-bonds), a secondary structure that is formed by oligomers with a 1:1 alternation of beta- and gamma-amino acid residues. Our characterization includes both crystallographic and 2D NMR data. Previous studies suggested that beta/gamma-peptides constructed from conformationally flexible residues adopt a different helical secondary structure in solution. Our design features preorganized beta- and gamma-residues, which strongly promote 13-helical folding by the 1:1 beta/gamma backbone.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amino Acids / analysis
  • Amino Acids / chemistry
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Models, Molecular
  • Peptides / chemistry*
  • Peptides / metabolism
  • Protein Folding*
  • Protein Structure, Secondary
  • Solutions

Substances

  • Amino Acids
  • Peptides
  • Solutions