Issue 19, 2009
From the journal:

Organic & Biomolecular Chemistry

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

Nicola Steffan,a   Alexander Grundmann,a   Shamil Afiyatullov,b   Hanli Ruanc  and  Shu-Ming Li*a  

* Corresponding authors

a Philipps-Universität Marburg, Institut für Pharmazeutische Biologie, Deutschhausstrasse 17A, Marburg, Germany
E-mail: shuming.li@Staff.uni-Marburg.de
Fax: +49-6421-2825365
Tel: +49-6421-2822461

b Pacific Institute of Bioorganic Chemistry, Far-East Division, Russian Academy of Sciences, pr. 100-letiya Vladivostoka, 159, Vladivistok, Russia

c Huazhong University of Science and Technology, Faculty of Pharmacy, Tongji Medical College, Hangkong Road 13, Wuhan, China

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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Article information

DOI
https://doi.org/10.1039/B908392H
Article type
Paper
Submitted
29 Apr 2009
Accepted
03 Jul 2009
First published
06 Aug 2009

Org. Biomol. Chem., 2009,7, 4082-4087

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

N. Steffan, A. Grundmann, S. Afiyatullov, H. Ruan and S. Li, Org. Biomol. Chem., 2009, 7, 4082 DOI: 10.1039/B908392H

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