Isolation, structure, and antibacterial activity of thiazomycin A, a potent thiazolyl peptide antibiotic from Amycolatopsis fastidiosa

Bioorg Med Chem. 2008 Oct 1;16(19):8818-23. doi: 10.1016/j.bmc.2008.08.079. Epub 2008 Sep 6.

Abstract

Thiazolyl peptides are a class of thiazole-rich macrocyclic potent antibacterial agents. Recently, we described thiazomycin, a new member of thiazolyl peptides, discovered by a thiazolyl peptide specific chemical screening. This method also allowed for the discovery of a new thiazolyl peptide, thiazomycin A, which carries modification in the oxazolidine ring of the amino sugar moiety. Thiazomycin A is a specific inhibitor of protein synthesis (IC(50) 0.7 microg/mL) and a potent Gram-positive antibacterial agent with minimum inhibitory concentration (MIC) ranging 0.002-0.25 microg/mL. The isolation and structure elucidation and biological activities of thiazomycin A are described.

MeSH terms

  • Actinomycetales / chemistry*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Inhibitory Concentration 50
  • Microbial Sensitivity Tests
  • Oxazoles / chemistry
  • Oxazoles / pharmacology
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification
  • Peptides, Cyclic / pharmacology*
  • Staphylococcus aureus / drug effects*
  • Staphylococcus aureus / growth & development
  • Thiazoles / chemistry
  • Thiazoles / isolation & purification
  • Thiazoles / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Oxazoles
  • Peptides, Cyclic
  • Thiazoles
  • thiazomycin
  • thiazomycin A
  • oxazolidine