Synthesis and biological evaluation of a MraY selective analogue of tunicamycins

Nucleosides Nucleotides Nucleic Acids. 2020;39(1-3):349-364. doi: 10.1080/15257770.2019.1649696. Epub 2019 Sep 30.

Abstract

Tunicamycins, which are nucleoside natural products, inhibit both bacterial phospho-N-acetylmuraminic acid (MurNAc)-pentapeptide translocase (MraY) and human UDP-N-acetylglucosamine (GlcNAc): polyprenol phosphate translocase (GPT). The improved synthesis and detailed biological evaluation of an MraY-selective inhibitor, 2, where the GlcNAc moiety was modified to a MurNAc amide, has been described.

Keywords: antibacterial; nucleoside natural products; organic chemistry.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology*
  • Bacterial Proteins / antagonists & inhibitors*
  • Bacterial Proteins / chemistry
  • Cell Line
  • Chemistry Techniques, Synthetic
  • Humans
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Structure-Activity Relationship
  • Transferases (Other Substituted Phosphate Groups)
  • Transferases / antagonists & inhibitors*
  • Transferases / chemistry
  • Tunicamycin / chemical synthesis*
  • Tunicamycin / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Bacterial Proteins
  • Tunicamycin
  • Transferases
  • Transferases (Other Substituted Phosphate Groups)
  • mraY protein, Bacteria