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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).
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