Orthanilic acid-promoted reverse turn formation in peptides

Chem Commun (Camb). 2013 Mar 18;49(22):2222-4. doi: 10.1039/c3cc40522b.

Abstract

Orthanilic acid (2-aminobenzenesulfonic acid, (S)Ant), an aromatic β-amino acid, has been shown to be highly useful in inducing a folded conformation in peptides. When incorporated into peptide sequences (Xaa-(S)Ant-Yaa), this rigid aromatic β-amino acid strongly imparts a reverse-turn conformation to the peptide backbone, featuring robust 11-membered-ring hydrogen-bonding.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Structure
  • Peptides / chemistry*
  • Protein Conformation
  • Sulfanilic Acids / chemistry*

Substances

  • Peptides
  • Sulfanilic Acids
  • 2-sulfanilic acid