Binaphthyl-anchored antibacterial tripeptide derivatives with hydrophobic C-terminal amino acid variations

John B. Bremner, Paul A. Keller, Stephen G. Pyne, Mark J. Robertson, K. Sakthivel, Kittiya Somphol, Dean Baylis, Jonathan A. Coates, John Deadman, Dharshini Jeevarajah, David I. Rhodes

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5 Citations (Scopus)

Abstract

The facile synthesis of seven new dicationic tripeptide benzyl ester derivatives, with hydrophobic group variations in the C-terminal amino acid component, is described. Moderate to good activity was seen against Gram-positive bacteria in vitro. One cyclohexylsubstituted compound 2c was tested more widely and showed good potency (MIC values ranging from 2-4 μg/mL) against antibiotic-resistant strains of Staphylococcus aureus and Enterococci (VRE, VSE), and against Staphylococcus epidermidis.

Original languageEnglish
Pages (from-to)1265-1270
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume8
DOIs
Publication statusPublished - 9 Aug 2012
Externally publishedYes

Keywords

  • Antibacterials
  • Binaphthyls
  • Cationic peptides
  • Peptides
  • Resistance
  • VISA
  • VRE

Cite this

Bremner, J. B., Keller, P. A., Pyne, S. G., Robertson, M. J., Sakthivel, K., Somphol, K., Baylis, D., Coates, J. A., Deadman, J., Jeevarajah, D., & Rhodes, D. I. (2012). Binaphthyl-anchored antibacterial tripeptide derivatives with hydrophobic C-terminal amino acid variations. Beilstein Journal of Organic Chemistry, 8, 1265-1270. https://doi.org/10.3762/bjoc.8.142