Gram-scale total synthesis of teixobactin promoting binding mode study and discovery of more potent antibiotics

Nat Commun. 2019 Jul 22;10(1):3268. doi: 10.1038/s41467-019-11211-y.

Abstract

Teixobactin represents a new class of antibiotics with novel structure and excellent activity against Gram-positive pathogens and Mycobacterium tuberculosis. Herein, we report a one-pot reaction to conveniently construct the key building block L-allo-Enduracidine in 30-gram scale in just one hour and a convergent strategy (3 + 2 + 6) to accomplish a gram-scale total synthesis of teixobactin. Several analogs are described, with 20 and 26 identified as the most efficacious analogs with 3~8-fold and 2~4-fold greater potency against vancomycin resistant Enterococcus faecalis and methicillin-resistant Staphylococcus aureus respectively in comparison with teixobactin. In addition, they show high efficiency in Streptococcus pneumoniae septicemia mouse model and neutropenic mouse thigh infection model using methicillin-resistant Staphylococcus aureus. We also propose that the antiparallel β-sheet of teixobactin is important for its bioactivity and an antiparallel dimer of teixobactin is the minimal binding unit for lipid II via key amino acids variations and molecular docking.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Cell Line, Tumor
  • Depsipeptides / chemical synthesis
  • Depsipeptides / chemistry
  • Depsipeptides / pharmacology*
  • Hep G2 Cells
  • Humans
  • Mice
  • Microbial Sensitivity Tests / methods*
  • Models, Chemical
  • Molecular Docking Simulation
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects
  • Pneumonia, Staphylococcal / drug therapy*
  • Pneumonia, Staphylococcal / microbiology
  • Staphylococcus aureus / drug effects*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Depsipeptides
  • teixobactin