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Issue 10, 2014
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Synthesis of full length and truncated microcin B17 analogues as DNA gyrase poisons

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Abstract

Microcin B17 (MccB17) is a post-translationally modified peptide containing thiazole and oxazole heterocycles that interrupt the peptide backbone. MccB17 is capable of poisoning DNA gyrase through stabilization of the gyrase-DNA cleavage complex and has therefore attracted significant attention. Using a combination of Fmoc-strategy solid-phase peptide synthesis and solution-phase fragment assembly we have prepared a library of full-length and truncated MccB17 analogues to investigate key structural requirements for gyrase-poisoning activity. Synthetic peptides lacking the glycine-rich N-terminal portion of the full-length sequence showed strong stabilization of the gyrase-DNA cleavage complex with increased potency relative to the full-length sequences. This truncation, however, led to a decrease in antibacterial activity of these analogues relative to their full-length counterparts indicating a potential role of the N-terminal region of the natural product for cellular uptake.

Graphical abstract: Synthesis of full length and truncated microcin B17 analogues as DNA gyrase poisons

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Supplementary files

Article information


Submitted
16 Dec 2013
Accepted
13 Jan 2014
First published
14 Jan 2014

Org. Biomol. Chem., 2014,12, 1570-1578
Article type
Paper
Author version available

Synthesis of full length and truncated microcin B17 analogues as DNA gyrase poisons

R. E. Thompson, F. Collin, A. Maxwell, K. A. Jolliffe and R. J. Payne, Org. Biomol. Chem., 2014, 12, 1570
DOI: 10.1039/C3OB42516A

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