Synthesis and antimicrobial activity of α-aminoboronic-containing peptidomimetics

J Pept Sci. 2014 Jan;20(1):20-4. doi: 10.1002/psc.2583. Epub 2013 Nov 13.

Abstract

A library of 175 dipeptidomimetics and tripeptidomimetics containing an α-amino boronic acid or boronate has been synthesized, and the activity toward Mycobacterium tuberculosis, Candida albicans, Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli and Pseudomonas aeruginosa has been screened. Although there is no clear structure-activity relationship, several compounds exhibit promising activity against different pathogens.

Keywords: Matteson homologation; antimicrobials; α-amino boronate; α-amino boronic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / pharmacology*
  • Boronic Acids / chemical synthesis
  • Boronic Acids / pharmacology*
  • Candida albicans / drug effects
  • Escherichia coli / drug effects
  • Hep G2 Cells
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Mimicry
  • Mycobacterium tuberculosis / drug effects
  • Peptidomimetics / chemical synthesis
  • Peptidomimetics / pharmacology*
  • Pseudomonas aeruginosa / drug effects
  • Staphylococcus aureus / drug effects
  • Streptococcus pyogenes / drug effects
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Boronic Acids
  • Peptidomimetics