Synthesis of triazole-functionalized 2-DOS analogues and their evaluation as A-site binders

Bioorg Med Chem Lett. 2014 Feb 15;24(4):1122-6. doi: 10.1016/j.bmcl.2013.12.125. Epub 2014 Jan 9.

Abstract

Aminoglycoside-antibiotics represent important tools for studying the biological functions of RNA. An orthogonal protection strategy applied on 2-deoxystreptamine (2-DOS) revealed a series of key intermediates that enable its regioselective functionalization. Our approach allowed the construction of selected representatives of triazole-containing analogues with diverse molecular frameworks for biological evaluation regarding their binding and antibacterial potencies.

Keywords: 2-Deoxystreptamine; Aminoglycosides; Orthogonal protection strategy; RNA recognition; Ribosomal A-site.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Dose-Response Relationship, Drug
  • Escherichia coli / drug effects*
  • Hexosamines / chemical synthesis
  • Hexosamines / chemistry
  • Hexosamines / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Pseudomonas aeruginosa / drug effects*
  • Staphylococcus aureus / drug effects*
  • Structure-Activity Relationship
  • Triazoles / chemistry*

Substances

  • Anti-Bacterial Agents
  • Hexosamines
  • Triazoles
  • 2-deoxystreptamine