Oxidation of lanthionines renders the lantibiotic nisin inactive.

Applied and Environmental Microbiology
Shawanda Wilson-StanfordLeif Smith

Abstract

The peptide antibiotic nisin A belongs to the group of antibiotics called lantibiotics. They are classified as lantibiotics because they contain the structural group lanthionine. Lanthionines are composed of a single sulfur atom that is linked to the beta-carbons of two alanine moieties. These sulfur atoms are vulnerable to environmental oxidation. A mild oxidation reaction was performed on nisin A to determine the relative effects it would have on bioactivity. High-mass-accuracy Fourier transform ion cyclotron resonance mass spectrometry data revealed the addition of seven, eight, and nine oxygens. These additions correspond to the five lanthionines, two methionines, and two histidines that would be susceptible to oxidation. Subsequent bioassays revealed that the oxidized form of nisin A had a complete loss of bactericidal activity. In a competition study, the oxidized nisin did not appear to have an antagonistic affect on the bioactivity of nisin A, since the addition of an equal molar concentration of the oxidized variant did not have an influence on the bactericidal activity of the native antibiotic. Electron microscopy data revealed that the oxidized forms were still capable of assembling into large circular complexes, dem...Continue Reading

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Apr 28, 2011·ACS Chemical Biology·Patrick J KnerrJohn D Lambris
Jun 13, 2012·Antimicrobial Agents and Chemotherapy·Aline Dias PaivaHilário Cuquetto Mantovani
Apr 23, 2013·Applied and Environmental Microbiology·Shaorong ChenLeif Smith
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Dec 23, 2017·Applied and Environmental Microbiology·Mengxin GengLeif Smith
May 20, 2018·Applied and Environmental Microbiology·Mengxin Geng, Leif Smith
May 14, 2017·Applied and Environmental Microbiology·Jerome EscanoLeif Smith
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Mar 9, 2017·Microbiology·Karen Machado GomesMaria do Carmo de Freire Bastos
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