FtmOx1, a non-heme Fe(ii) and α-ketoglutarate-dependent dioxygenase, catalyses the endoperoxide formation of verruculogen in Aspergillus fumigatus?

Organic & Biomolecular Chemistry Pub Date: 2009-08-06 DOI: 10.1039/B908392H

Abstract

Verruculogen is a tremorgenic mycotoxin and contains an endoperoxide bond. In this study, we describe the cloning, overexpression and purification of a non-heme Fe(II) and α-ketoglutarate-dependent dioxygenase FtmOx1 from Aspergillus fumigatus, which catalyses the converstion of fumitremorgin B to verruculogen by inserting an endoperoxide bond between two prenyl moieties. Incubation with 18O2-enriched atmosphere demonstrated that both oxygen atoms of the endoperoxide bond are derived from one molecule of O2. FtmOx1 is the first endoperoxide-forming non-heme Fe(II) and α-ketoglutarate-dependent dioxygenase reported so far. A mechanism of FtmOx1-catalysed verruculogen formation is postulated and discussed.

Graphical abstract: FtmOx1, a non-heme Fe(ii) and α-ketoglutarate-dependent dioxygenase, catalyses the endoperoxide formation of verruculogen in Aspergillus fumigatus
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