Communication

Formation of the Pyridazine Natural Product Azamerone by Biosynthetic Rearrangement of an Aryl Diazoketone†

  1. Jaclyn M. Winter1,
  2. Ariane L. Jansma2,
  3. Tracy M. Handel Dr.2,
  4. Bradley S. Moore Dr.1,2

Article first published online: 15 DEC 2008

DOI: 10.1002/anie.200805140

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 48, Issue 4, pages 767–770, January 12, 2009

Additional Information

How to Cite

Winter, J., Jansma, A., Handel, T. and Moore, B. (2009), Formation of the Pyridazine Natural Product Azamerone by Biosynthetic Rearrangement of an Aryl Diazoketone. Angewandte Chemie International Edition, 48: 767–770. doi: 10.1002/anie.200805140

Author Information

  1. 1

    Scripps Institution of Oceanography, University of California at San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0204 (USA), Fax: (+1) 858-534-1305 http://moorelab.ucsd.edu

  2. 2

    Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California at San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)

  1. †

    This work was supported by the California Sea Grant Program (R/NMP-98 to B.S.M.) and by a Ruth L. Kirschstein National Research Service Award to J.M.W. from the NIH Training Program in Marine Biotechnology (GM067550). We thank Dr. W. Fenical, Dr. P. R. Jensen, Dr. H. C. Kwon, and Dr. J. Y. Cho (University of California at San Diego (USA)) for Streptomyces sp. CNQ-766 and standard azamerone, and Dr. R. J. Parry (Rice University (USA)), Dr. T. F. Molinski, Dr. T. A. M. Gulder, and Dr. A. A. Mrse for helpful advice.

Publication History

  1. Issue published online: 5 JAN 2009
  2. Article first published online: 15 DEC 2008
  3. Manuscript Received: 20 OCT 2008

Funded by

  • California Sea Grant Program. Grant Number: R/NMP-98
  • NIH. Grant Number: GM067550

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Keywords:

  • biosynthesis;
  • biotransformations;
  • isotopic labeling;
  • natural products;
  • nitrogen heterocycles

Graphical Abstract

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All in the family: Knowledge of the biosynthesis of N[BOND]N containing natural products is limited. Feeding experiments with 13C and 15N-labeled molecules establish that the phthalazinone core of azamerone is derived from the diazo chlorinated meroterpenoid SF2415A3. A biosynthetic mechanism involving an oxidative rearrangement of the aryl diazoketone followed by rearomatization with the dinitrogen group is proposed.

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