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Epidithiol Formation by an Unprecedented Twin Carbon–Sulfur Lyase in the Gliotoxin Pathway†

  1. Daniel H. Scharf1,‡,
  2. Pranatchareeya Chankhamjon1,‡,
  3. Dr. Kirstin Scherlach1,
  4. Dr. Thorsten Heinekamp1,
  5. Dr. Martin Roth1,
  6. Prof. Dr. Axel A. Brakhage1,2,
  7. Prof. Dr. Christian Hertweck1,2,*

Article first published online: 31 AUG 2012

DOI: 10.1002/anie.201205041

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 40, pages 10064–10068, October 1, 2012

Additional Information

How to Cite

Scharf, D. H., Chankhamjon, P., Scherlach, K., Heinekamp, T., Roth, M., Brakhage, A. A. and Hertweck, C. (2012), Epidithiol Formation by an Unprecedented Twin Carbon–Sulfur Lyase in the Gliotoxin Pathway . Angew. Chem. Int. Ed., 51: 10064–10068. doi: 10.1002/anie.201205041

Author Information

  1. 1

    Depts. of Biomolecular Chemistry, Molecular and Applied Microbiology, and Bio Pilot Plant, Leibniz Institute for Natural Product Research and Infection Biology, HKI, Beutenbergstrasse 11a, 07745 Jena (Germany)

  2. 2

    Friedrich Schiller University, Jena (Germany)

  1. ‡

    These authors contributed equally to this work.

*Depts. of Biomolecular Chemistry, Molecular and Applied Microbiology, and Bio Pilot Plant, Leibniz Institute for Natural Product Research and Infection Biology, HKI, Beutenbergstrasse 11a, 07745 Jena (Germany)

  1. †

    We thank A. Perner for MS measurements, S. Fricke and C. Schult for technical assistance, P. Hortschansky for artwork, and C. Heiden and P. Berthel for performing fermentations. This work was supported by the “Pakt für Forschung und Innovation” of the Free State of Thuringia and the BMBF, and the International Leibniz Research School for Biomolecular and Microbial Interactions (ILRS), as part of the excellence graduate school Jena School for Microbial Communication (JSMC).

  2. ‡

    These authors contributed equally to this work.

Publication History

  1. Issue published online: 26 SEP 2012
  2. Article first published online: 31 AUG 2012
  3. Manuscript Received: 27 JUN 2012

Funded by

  • Free State of Thuringia
  • BMBF
  • International Leibniz Research School for Biomolecular and Microbial Interactions (ILRS)

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Keywords:

  • Aspergillus fumigatus;
  • gliotoxin;
  • lyases;
  • mycotoxins;
  • organosulfur compounds
Thumbnail image of graphical abstract

Two in one go: The elucidation of a key step in the biosynthesis of gliotoxin, the infamous virulence factor of the human pathogen Aspergillus fumigatus, provides insight into the formation of an epidithiol. Isolation of a bis(cysteine) S-conjugate from a ΔgliI mutant and in vitro studies show that GliI concomitantly cleaves two C[BOND]S bonds, along with the formation of ammonia and pyruvate (see scheme).

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