Pyrrole Aminoimidazole Alkaloid Metabiosynthesis with Marine Sponges Agelas conifera and Stylissa caribica

Authors

  • Dr. E. Paige Stout,

    1. Department of Chemistry and Biochemistry and Skaggs School of Pharmacy and Pharmaceutical Science, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)
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  • Dr. Yong-Gang Wang,

    1. Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, TX 77842 (USA)
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  • Prof. Dr. Daniel Romo,

    1. Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, TX 77842 (USA)
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  • Prof. Dr. Tadeusz F. Molinski

    Corresponding author
    1. Department of Chemistry and Biochemistry and Skaggs School of Pharmacy and Pharmaceutical Science, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)
    • Department of Chemistry and Biochemistry and Skaggs School of Pharmacy and Pharmaceutical Science, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)
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  • Funding for this work from NIH (GM052964) and a Ruth L. Kirschstein National Research Service Award (NIH/NCI T32 CA009523) is gratefully acknowledged. We thank J. J. LaClair and M. Burkart for help with fluorescence spectra, B. Morinaka and Y. Su (UCSD) for NMR and HRMS measurements, respectively. We are grateful to J. Pawlik (UNC Wilmington), and the captain and crew of the RV Cape Hatteras for logistical support during collecting expeditions and in-field assays.

Abstract

original image

Game-SET-match: Pyrrole aminoimidazole alkaloids (PAIs) are metabiosynthesized from chlorinated analogues of oroidin by cell-free enzyme preparations from PAI-producing sponges. Evidence and implications for the biosynthesis of PAIs include putative single-electron transfers (SETs) that promote C[BOND]C bond-forming reactions of precursors.

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