Issue 12, 2022

Synthesis and structure–activity relationship studies of N-terminal analogues of the lipopeptide antibiotics brevicidine and laterocidine

Abstract

The brevicidine and laterocidine family of lipopeptide antibiotics exhibit strong activity against multidrug-resistant Gram-negative bacteria, while showing low propensity to induce resistance. Both peptides feature a branched lipid tail on the N-terminal residue, which for brevicidine is chiral. Here, we report the synthesis and biological evaluation of a library of brevicidine and laterocidine analogues wherein the N-terminal lipid is replaced with linear achiral fatty acids. Optimal lipid chain lengths were determined and new analogues with strong activity against colistin-resistant E. coli produced.

Graphical abstract: Synthesis and structure–activity relationship studies of N-terminal analogues of the lipopeptide antibiotics brevicidine and laterocidine

Supplementary files

Article information

Article type
Research Article
Submitted
17 Aug 2022
Accepted
26 Oct 2022
First published
27 Oct 2022
This article is Open Access
Creative Commons BY license

RSC Med. Chem., 2022,13, 1640-1643

Synthesis and structure–activity relationship studies of N-terminal analogues of the lipopeptide antibiotics brevicidine and laterocidine

R. D. Ballantine, K. Al Ayed, S. J. Bann, M. Hoekstra, N. I. Martin and S. A. Cochrane, RSC Med. Chem., 2022, 13, 1640 DOI: 10.1039/D2MD00281G

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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