Chemical Synthesis of Bioactive Naturally Derived Cyclic Peptides Containing Ene-Like Rigidifying Motifs

Chemistry. 2018 Dec 5;24(68):17869-17880. doi: 10.1002/chem.201802533. Epub 2018 Oct 18.

Abstract

The development of synthetic methods to prepare conformationally constrained peptides and peptide-polyketide hybrids remain an important chemical challenge. It is known that structural rigidity correlates with the specificity, bioactivity, and stability of these peptide systems, thus rigid systems are particularly attractive leads for development of potent biopharmaceuticals. Herein we provide an overview of recent developments in the syntheses of naturally derived constrained peptides and peptide-polyketide hybrids, with a particular emphasis on those systems containing an ene-like bond.

Keywords: (thio)enamide; cyclopeptides; imines; peptides; synthesis.

Publication types

  • Review

MeSH terms

  • Alkaloids / chemical synthesis
  • Alkaloids / chemistry
  • Alpha-Amanitin / chemical synthesis
  • Alpha-Amanitin / chemistry
  • Amino Acid Sequence
  • Amino Acids / chemical synthesis
  • Amino Acids / chemistry
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Imines / chemical synthesis
  • Imines / chemistry
  • Macrocyclic Compounds / chemical synthesis
  • Macrocyclic Compounds / chemistry
  • Molecular Conformation
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry
  • Polyketides / chemical synthesis*
  • Polyketides / chemistry
  • Solid-Phase Synthesis Techniques / methods*

Substances

  • Alkaloids
  • Alpha-Amanitin
  • Amino Acids
  • Biological Products
  • Imines
  • Macrocyclic Compounds
  • Peptides, Cyclic
  • Polyketides
  • nannocystin A