Total syntheses and biological evaluation of miuraenamides

Angew Chem Int Ed Engl. 2015 Apr 7;54(15):4502-7. doi: 10.1002/anie.201411212. Epub 2015 Feb 16.

Abstract

The miuraenamides, relatively simple representatives of a class of cyclodepsipeptides with high antitumor activity, can be easily and flexibly obtained by the concept of peptide modification. A reaction sequence consisting of an aldol reaction, oxidation, and methylation of the glycine subunit of the cyclodepsipeptides allows the incorporation of the unusual α,β-unsaturated dehydroamino acid in one of the last steps of the synthesis.

Keywords: actin-binding compounds; antitumor activity; cyclodepsipeptides; miuraenamides; natural products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Actins / metabolism
  • Actins / ultrastructure
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Depsipeptides / chemical synthesis
  • Depsipeptides / chemistry*
  • Depsipeptides / pharmacology*
  • Humans
  • Methylation
  • Neoplasms / drug therapy
  • Neoplasms / metabolism
  • Oxidation-Reduction

Substances

  • Actins
  • Antineoplastic Agents
  • Depsipeptides
  • miuraenamide A