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The sequence of the enterococcal cytolysin imparts unusual lanthionine stereochemistry

Nature Chemical Biology volume 9, pages 157–159 (2013)Cite this article

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Abstract

The enterococcal cytolysin is a two-component lantibiotic of unknown structure with hemolytic activity that is important for virulence. We prepared cytolysin by coexpression of each precursor peptide with the synthetase CylM in Escherichia coli and characterized its structure. Unexpectedly, cytolysin is to our knowledge the first example of a lantibiotic containing lanthionine and methyllanthionine structures with different stereochemistries in the same peptide. The stereochemistry is determined by the sequence of the substrate peptide.

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Figure 1: Structural analysis of CylM-modified CylLL and CylLS.
Figure 2: Structure of the enterococcal cytolysin determined in this work.
Figure 3: Alignment of seven lantibiotic core peptides, stereochemical analysis of Halβ and bioactivity of CylLL″ and CylLS″.

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Acknowledgements

We thank X. Yang (University of Illinois) for providing the modified HalA2 and Halβ peptides. This work was supported by the US National Institutes of Health (GM58822).

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Authors and Affiliations

  1. Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois, USA

    Weixin Tang & Wilfred A van der Donk

  2. Howard Hughes Medical Institute, University of Illinois at Urbana-Champaign, Urbana, Illinois, USA

    Weixin Tang & Wilfred A van der Donk

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  1. Weixin Tang
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  2. Wilfred A van der Donk
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Contributions

W.T. and W.A.v.d.D. designed the study. W.T. performed all experiments. W.T. and W.A.v.d.D. analyzed the data and wrote the manuscript.

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Correspondence to Wilfred A van der Donk.

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The authors declare no competing financial interests.

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Tang, W., van der Donk, W. The sequence of the enterococcal cytolysin imparts unusual lanthionine stereochemistry. Nat Chem Biol 9, 157–159 (2013). https://doi.org/10.1038/nchembio.1162

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