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

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  • 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.

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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