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

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

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 cyclohexyl-substituted compound 2c was tested more...

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Veröffentlicht in:Beilstein journal of organic chemistry 2012-08, Vol.8 (1), p.1265-1270
Hauptverfasser: Bremner, John B, Keller, Paul A, Pyne, Stephen G, Robertson, Mark J, Sakthivel, K, Somphol, Kittiya, Baylis, Dean, Coates, Jonathan A, Deadman, John, Jeevarajah, Dharshini, Rhodes, David I
Format: Artikel
Sprache:eng
Schlagworte:
antibacterials
binaphthyls
cationic peptides
Chemistry
Full Research Paper
peptides
resistance
VISA
VRE
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Zusammenfassung: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 cyclohexyl-substituted 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.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.8.142