Clathrodin, oroidin and hymenidin belong to a family of pyrrole amino-imidazole (PAI) alkaloids, isolated from marine sponges. The primary importance of these molecules stems from their status as the presumed simple precursors to more complex PAIs known to exhibit potent antibacterial and antitumor properties.Using cell-free enzyme preparations of the marine sponges Agelas conifera and Stylissa caribica with unnatural, chlorinated clathrodin substrates the first direct insights into the biosynthetic pathways employed by these organisms have been elucidated. This study seeks to further this investigation through the synthesis of additional clathrodin derivatives with nitro, amine, azide and alkyne substituents, for use as biosynthetic precursors. The results will enable further understanding of the mechanistic details of the conversion from the simple precursors to the more complex PAI's and potentially assist in isolation of the biosynthetic enzyme(s) involved in these biotransformations.Reference: (1) Y.-G. Wang, B. I. Morinaka, J. C. P. Reyes, J. J. Wolff, D. Romo and T. F. Molinski, Journal of Natural Products 2010  , 73, 428-434.

Investigating the cell-free 'metabiosynthesis' of pyrrole-2-aminoimidazole alkaloids as novel biosynthetic precursors, clathrodin derivatives

243rd National Meeting (2012)

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