Peptides containing β-amino acid patterns: challenges and successes in medicinal chemistry

J Med Chem. 2014 Dec 11;57(23):9718-39. doi: 10.1021/jm5010896. Epub 2014 Sep 24.

Abstract

The construction of bioactive peptides using β-amino acid-containing sequence patterns is a very promising strategy to obtain analogues that exhibit properties of high interest for medicinal chemistry applications. β-Amino acids have been shown to modulate the conformation, dynamics, and proteolytic susceptibility of native peptides. They can be either combined with α-amino acids by following specific patterns, which results in backbone architectures with well-defined orientations of the side chain functional groups, or assembled in de novo-designed bioactive β- or α,β-peptidic sequences. Such peptides display various biological functions, including antimicrobial activity, inhibition of protein-protein interactions, agonism/antagonism of GPCR ligands, and anti-angiogenic activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Amino Acids / chemistry
  • Humans
  • Ligands
  • Peptides / chemistry*
  • Protein Conformation
  • Protein Structure, Secondary
  • Receptors, LHRH / chemistry
  • Receptors, Vascular Endothelial Growth Factor / chemistry
  • Stereoisomerism

Substances

  • Amino Acids
  • GNRHR protein, human
  • Ligands
  • Peptides
  • Receptors, LHRH
  • Receptors, Vascular Endothelial Growth Factor