Carboxamide versus sulfonamide in peptide backbone folding: a case study with a hetero foldamer

Org Lett. 2013 Apr 5;15(7):1504-7. doi: 10.1021/ol4002762. Epub 2013 Mar 8.

Abstract

Strikingly dissimilar hydrogen-bonding patterns have been observed for two sets of closely similar hetero foldamers containing carboxamide and sulfonamides at regular intervals. Although both foldamers maintain conformational ordering, the hydrogen-bonding pattern and backbone helical handedness differ diametrically.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Amino Acid Sequence
  • Amino Acids / chemistry
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Protein Structure, Secondary
  • Sulfonamides / chemistry*

Substances

  • Amides
  • Amino Acids
  • Peptides
  • Sulfonamides