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

Bremner, John B., Keller, Paul A., Pyne, Stephen G., Robertson, Mark, Sakthivel, K., Somphol, Kittiya, Baylis, Dean, Coates, Jonathan A., Deadman, John, Jeevarajah, Dharshini, and Rhodes, David I. (2012) Binaphthyl-anchored antibacterial tripeptide derivatives with hydrophobic C-terminal amino acid variations. Beilstein Journal of Organic Chemistry, 8. pp. 1265-1270.

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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 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.

Item ID: 36835
Item Type: Article (Refereed Research - C1)
Keywords: antibacterials, binaphthyls, cationic peptides, peptides, resistance, VISA, VRE
Additional Information:

Copyright © 2012 Bremner et al; licensee Beilstein-Institut.

This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)

ISSN: 1860-5397
Date Deposited: 10 Dec 2014 07:31
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 100%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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