Highly functionalized cyclic β-amino acid moieties as promising scaffolds in peptide research and drug design

Amino Acids. 2017 Sep;49(9):1441-1455. doi: 10.1007/s00726-017-2439-9. Epub 2017 May 30.

Abstract

Peptide-based drug research has received high attention in the field of medicinal chemistry over the past decade. For drug design, to improve proteolytic stability, it is desirable to include unnatural building blocks, such as conformationally restricted β-amino acid moieties, into the peptide sequence. Accordingly, the synthesis and incorporation of such conformationally rigid systems into novel type of peptides has gained large interest. Our research group has designed highly efficient methods for the construction of potential antimicrobial peptides. Moreover, a number of synthetic approaches have been developed for the synthesis of various pharmacologically interesting cyclic β-amino acid derivatives as monomers with multiple stereogenic centers.

Keywords: Building blocks; Functionalization; Peptide synthesis; Peptidomimetics; β-Amino acids.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Amino Acid Sequence
  • Amino Acids, Cyclic / chemistry*
  • Antimicrobial Cationic Peptides / chemical synthesis*
  • Chemistry, Pharmaceutical
  • Combinatorial Chemistry Techniques
  • Drug Design*
  • Humans
  • Peptides / chemical synthesis*
  • Peptidomimetics / chemical synthesis*
  • Protein Structure, Secondary

Substances

  • Amino Acids, Cyclic
  • Antimicrobial Cationic Peptides
  • Peptides
  • Peptidomimetics