Synthesis and Biological Evaluation of a Teixobactin Analogue

Org Lett. 2015 Dec 18;17(24):6182-5. doi: 10.1021/acs.orglett.5b03176. Epub 2015 Dec 10.

Abstract

The first synthesis and biological activity of a teixobactin analogue is reported. Substitution of the unusual L-allo-enduracididine residue by the naturally occurring L-arginine was achieved, and the analogue gave an activity trend similar to that of teixobactin (against Gram-postive bacteria) and meropenem, which was approved by the FDA in 1996. The synthetic route used allows for the synthesis of the natural product as well as the development of a program of medicinal chemistry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arginine / chemistry
  • Biological Products / chemistry
  • Depsipeptides / chemical synthesis*
  • Depsipeptides / chemistry
  • Depsipeptides / pharmacology*
  • Meropenem
  • Molecular Structure
  • Stereoisomerism
  • Thienamycins / pharmacology

Substances

  • Biological Products
  • Depsipeptides
  • Thienamycins
  • Arginine
  • Meropenem
  • teixobactin