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The gyrase inhibitor albicidin consists of p-aminobenzoic acids and cyanoalanine

Nature Chemical Biology volume 11, pages 195–197 (2015)Cite this article

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Abstract

Albicidin is a potent DNA gyrase inhibitor produced by the sugarcane pathogenic bacterium Xanthomonas albilineans. Here we report the elucidation of the hitherto unknown structure of albicidin, revealing a unique polyaromatic oligopeptide mainly composed of p-aminobenzoic acids. In vitro studies provide further insights into the biosynthetic machinery of albicidin. These findings will enable structural investigations on the inhibition mechanism of albicidin and its assessment as a highly effective antibacterial drug.

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Figure 1: Structural characterization of albicidin.
Figure 2: Model of albicidin biosynthesis.

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References

  1. Young, J.M., Park, D.C., Shearman, H.M. & Fargier, E. Syst. Appl. Microbiol. 31, 366–377 (2008).

    Article  CAS  Google Scholar 

  2. Royer, M. et al. Mol. Plant Microbe Interact. 17, 414–427 (2004).

    Article  CAS  Google Scholar 

  3. Dal-Bianco, M. et al. Curr. Opin. Biotechnol. 23, 265–270 (2012).

    Article  CAS  Google Scholar 

  4. Birch, R.G. & Patil, S.S. Phytopathology 73, 1368–1374 (1983).

    Article  Google Scholar 

  5. Birch, R.G. & Patil, S.S. Physiol. Mol. Plant Pathol. 30, 207–214 (1987).

    Article  CAS  Google Scholar 

  6. Birch, R.G. & Patil, S.S. Physiol. Mol. Plant Pathol. 30, 199–206 (1987).

    Article  CAS  Google Scholar 

  7. Birch, R.G. & Patil, S.S. Antibiotic and process for the production thereof. US patent 4,525,354 (1985).

  8. Hashimi, S.M., Wall, M.K., Smith, A.B., Maxwell, A. & Birch, R.G. Antimicrob. Agents Chemother. 51, 181–187 (2007).

    Article  CAS  Google Scholar 

  9. Corbett, K.D. & Berger, J.M. Annu. Rev. Biophys. Biomol. Struct. 33, 95–118 (2004).

    Article  CAS  Google Scholar 

  10. Maxwell, A. & Lawson, D.M. Curr. Top. Med. Chem. 3, 283–303 (2003).

    Article  CAS  Google Scholar 

  11. Vivien, E. et al. Antimicrob. Agents Chemother. 51, 1549–1552 (2007).

    Article  CAS  Google Scholar 

  12. Dosselaere, F. & Vanderleyden, J. Crit. Rev. Microbiol. 27, 75–131 (2001).

    Article  CAS  Google Scholar 

  13. Stachelhaus, T. & Marahiel, M.A. FEMS Microbiol. Lett. 125, 3–14 (1995).

    Article  CAS  Google Scholar 

  14. Du, L., Sanchez, C., Chen, M., Edwards, D.J. & Shen, B. Chem. Biol. 7, 623–642 (2000).

    Article  CAS  Google Scholar 

  15. Aravind, L., Anantharaman, V. & Koonin, E.V. Proteins 48, 1–14 (2002).

    Article  CAS  Google Scholar 

  16. Huang, G., Zhang, L. & Birch, R.G. Gene 255, 327–333 (2000).

    Article  CAS  Google Scholar 

  17. Koglin, A. et al. Science 312, 273–276 (2006).

    Article  CAS  Google Scholar 

  18. Tanovic, A., Samel, S.A., Essen, L.O. & Marahiel, M.A. Science 321, 659–663 (2008).

    Article  CAS  Google Scholar 

  19. Stachelhaus, T., Mootz, H.D. & Marahiel, M.A. Chem. Biol. 6, 493–505 (1999).

    Article  CAS  Google Scholar 

  20. Birch, R.G. & Patil, S.S. J. Gen. Microbiol. 131, 1069–1075 (1985).

    CAS  PubMed  Google Scholar 

  21. Zhang, L., Xu, J. & Birch, R.G. J. Appl. Microbiol. 85, 1023–1028 (1998).

    Article  CAS  Google Scholar 

  22. Altschul, S.F., Gish, W., Miller, W., Myers, E.W. & Lipman, D.J. J. Mol. Biol. 215, 403–410 (1990).

    Article  CAS  Google Scholar 

  23. McWilliam, H. et al. Nucleic Acids Res. 41, W597–W600 (2013).

    Article  Google Scholar 

  24. Bachmann, B.O. & Ravel, J. Methods Enzymol. 458, 181–217 (2009).

    Article  CAS  Google Scholar 

  25. Zhang, Y. BMC Bioinformatics 9, 40 (2008).

    Article  Google Scholar 

  26. Bogomolovas, J., Simon, B., Sattler, M. & Stier, G. Protein Expr. Purif. 64, 16–23 (2009).

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by a grant from the Deutsche Forschungsgemeinschaft (DFG SU239/11-1; SU 18-1), by the Cluster of Excellence 'Unifying Concepts in Catalysis (UniCat)' (DFG) and by a grant from the Agence Nationale de la Recherche (ANR-09-BLAN-0413-01).

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Author notes

  1. Stéphane Cociancich, Alexander Pesic and Daniel Petras: These authors contributed equally to this work.

Authors and Affiliations

  1. Cirad, UMR Biologie et Génétique des Interactions Plante-Parasite, Montpellier, France

    Stéphane Cociancich, Sandrine Duplan, Mélanie Marguerettaz, Julie Noëll, Isabelle Pieretti, Philippe Rott & Monique Royer

  2. Institut für Chemie, Technische Universität Berlin, Berlin, Germany

    Alexander Pesic, Daniel Petras, Stefanie Uhlmann, Julian Kretz, Vivien Schubert, Laura Vieweg, Manuela Hügelland, Sebastian Kemper, Andi Mainz & Roderich D Süssmuth

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  1. Stéphane Cociancich
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  2. Alexander Pesic
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Contributions

S.C., A.P., S.D., M.M., J.N., I.P., M.H., P.R. and M.R. performed the cultivation and isolation of albicidin. A.P., D.P., V.S., S.K. and A.M. performed the structural elucidation of albicidin. D.P., S.U., A.M. and M.R. performed the bioinformatic analysis of the biosynthesis genes. D.P., S.U. and M.H. produced the proteins and performed the in vitro assays. J.K. synthetized the substrates for the in vitro assay. S.C., A.P., D.P., A.M., M.R. and R.D.S. designed the study and analyzed the data. S.C., A.P., D.P., L.V., A.M., M.R. and R.D.S. wrote the manuscript.

Corresponding authors

Correspondence to Monique Royer or Roderich D Süssmuth.

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The authors declare no competing financial interests.

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Supplementary Results, Supplementary Tables 1–6 and Supplementary Figures 1–12. (PDF 2134 kb)

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Cociancich, S., Pesic, A., Petras, D. et al. The gyrase inhibitor albicidin consists of p-aminobenzoic acids and cyanoalanine. Nat Chem Biol 11, 195–197 (2015). https://doi.org/10.1038/nchembio.1734

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