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. 2012 May 14;51(20):4877-81.
doi: 10.1002/anie.201108119. Epub 2012 Apr 4.

Pyrrole aminoimidazole alkaloid metabiosynthesis with marine sponges Agelas conifera and Stylissa caribica

E Paige Stout  1 , Yong-Gang Wang, Daniel Romo, Tadeusz F Molinski
Affiliations

Pyrrole aminoimidazole alkaloid metabiosynthesis with marine sponges Agelas conifera and Stylissa caribica

E Paige Stout et al. Angew Chem Int Ed Engl. .

Abstract

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-C bond-forming reactions of precursors.

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Figures

Figure 1
Figure 1
Representative PAIs from sponges Agelas spp. and Stylissa, and unnatural chlorinated analogs (3d,e, 4d).
Scheme 1
Scheme 1
Structures of nagelamide H (7a) and chlorinated products 6, 7d, 8 obtained from cell-free metabiosynthesis of 3d and base promoted elimination of 8 to 4d.
Scheme 2
Scheme 2
Proposed mechanisms for enzyme-catalyed SET of 3d and cyclization to 1a (path a) or 6/8 (path b).
See this image and copyright information in PMC

References

    1. For clarity, each PAI is drawn as the free base and a discrete tautomer, although most are isolated as salts, and counterions and tautomer equilibria may vary with structure.

    1. Aiello A, Fattorusso E, Menna M, Taglialatela-Scafati O, Fattorusso E. Modern Alkaloids. In: Taglialatela-Scafati O, editor. Structure, Isolation, Synthesis, and Biology. WILEY-VCH; Darmstadt: 2008. The possibility that PAIs are the products of bacterial consortia has not been excluded.

    1. Walker RP, Faulkner DJ, Van Engen D, Clardy J. J. Am. Chem. Soc. 1981;103:6772–6773.
    1. Bernan VS, Roll DM, Ireland CM, Greenstein M, Maiese WM, Steinberg DA. J. Antimicrob. Chemother. 1993;32:539–550. - PubMed
    2. Rosa R, Silva W, de Motta GE, Rodríguez AD, Morales JJ, Ortiz M. - PubMed
    3. Rodríguez AD, Lear MJ, Clair J.J. La. J. Am. Chem. Soc. 2008;130:7256–7258. - PubMed
    4. Cipres A, O’Malley DP, Li K, Finlay D, Baran PS, Vuori K. ACS Chem. Biol. 2010;5:195–202. - PMC - PubMed
    1. Kobayashi J, Ohizumi Y, Nakamura H, Hirata Y. Experientia. 1986;42:1176–1177. - PubMed

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