Frontier Between Cyclic Peptides and Macrocycles

Methods Mol Biol. 2019:2001:147-202. doi: 10.1007/978-1-4939-9504-2_9.

Abstract

This review describes a selection of macrocyclic natural products and structurally modified analogs containing peptidic and non-peptidic elements as structural features that potentially modulate cellular permeability. Examples range from exclusively peptidic structures like cyclosporin A or phepropeptins to compounds with mostly non-peptidic character, such as telomestatin or largazole. Furthermore, semisynthetic approaches and synthesis platforms to generate general and focused libraries of compounds at the interface of cyclic peptides and non-peptidic macrocycles are discussed.

Keywords: Cellular permeability; Library; Macrocycle; Modular synthesis; Semi-synthesis.

Publication types

  • Review

MeSH terms

  • Biological Products
  • Cyclization
  • Depsipeptides / chemistry
  • Depsipeptides / metabolism
  • Humans
  • Lactones / chemistry
  • Lactones / metabolism
  • Macrocyclic Compounds / chemical synthesis
  • Macrocyclic Compounds / chemistry*
  • Oxazoles / chemistry
  • Oxazoles / metabolism
  • Peptide Library
  • Peptides, Cyclic / chemical synthesis
  • Peptides, Cyclic / chemistry*
  • Peptides, Cyclic / metabolism
  • Permeability
  • Protein Conformation
  • Spiro Compounds / chemistry
  • Spiro Compounds / metabolism
  • Streptogramins / chemistry
  • Streptogramins / metabolism
  • Thiazoles / chemistry
  • Thiazoles / metabolism

Substances

  • Biological Products
  • Depsipeptides
  • Lactones
  • Macrocyclic Compounds
  • Oxazoles
  • Peptide Library
  • Peptides, Cyclic
  • Spiro Compounds
  • Streptogramins
  • Thiazoles
  • apratoxin A
  • largazole
  • sanglifehrin A
  • telomestatin
  • jasplakinolide