FtmOx1, a non-heme Fe(II) and alpha-ketoglutarate-dependent dioxygenase, catalyses the endoperoxide formation of verruculogen in Aspergillus fumigatus
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 alpha-ketoglutarate-dependent dioxygenase FtmOx1 from Aspergillus fumigatus, which catalyses the conversion of fumitremorgin B t...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2009-01, Vol.7 (19), p.4082-4087 |
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| container_issue | 19 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Steffan, Nicola Grundmann, Alexander Afiyatullov, Shamil Ruan, Hanli Li, Shu-Ming |
| description | 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 alpha-ketoglutarate-dependent dioxygenase FtmOx1 from Aspergillus fumigatus, which catalyses the conversion of fumitremorgin B to verruculogen by inserting an endoperoxide bond between two prenyl moieties. Incubation with (18)O(2)-enriched atmosphere demonstrated that both oxygen atoms of the endoperoxide bond are derived from one molecule of O(2). FtmOx1 is the first endoperoxide-forming non-heme Fe(ii) and alpha-ketoglutarate-dependent dioxygenase reported so far. A mechanism of FtmOx1-catalysed verruculogen formation is postulated and discussed. |
| doi_str_mv | 10.1039/b908392h |
| format | Article |
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In this study, we describe the cloning, overexpression and purification of a non-heme Fe(ii) and alpha-ketoglutarate-dependent dioxygenase FtmOx1 from Aspergillus fumigatus, which catalyses the conversion of fumitremorgin B to verruculogen by inserting an endoperoxide bond between two prenyl moieties. Incubation with (18)O(2)-enriched atmosphere demonstrated that both oxygen atoms of the endoperoxide bond are derived from one molecule of O(2). FtmOx1 is the first endoperoxide-forming non-heme Fe(ii) and alpha-ketoglutarate-dependent dioxygenase reported so far. A mechanism of FtmOx1-catalysed verruculogen formation is postulated and discussed.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/b908392h</identifier><identifier>PMID: 19763315</identifier><language>eng</language><publisher>England</publisher><subject>Aspergillus fumigatus - enzymology ; Biocatalysis ; Chromatography, High Pressure Liquid ; Dioxygenases - chemistry ; Dioxygenases - metabolism ; Heme ; Indoles - chemistry ; Indoles - metabolism ; Iron - metabolism ; Ketoglutaric Acids - metabolism ; Peroxides - chemistry ; Spectrometry, Mass, Electrospray Ionization</subject><ispartof>Organic & biomolecular chemistry, 2009-01, Vol.7 (19), p.4082-4087</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c282t-e8acdf3fea94d6d8d0e4c9fa2b42d74037224d6370b70cade6f8210e34d192303</citedby><cites>FETCH-LOGICAL-c282t-e8acdf3fea94d6d8d0e4c9fa2b42d74037224d6370b70cade6f8210e34d192303</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19763315$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Steffan, Nicola</creatorcontrib><creatorcontrib>Grundmann, Alexander</creatorcontrib><creatorcontrib>Afiyatullov, Shamil</creatorcontrib><creatorcontrib>Ruan, Hanli</creatorcontrib><creatorcontrib>Li, Shu-Ming</creatorcontrib><title>FtmOx1, a non-heme Fe(II) and alpha-ketoglutarate-dependent dioxygenase, catalyses the endoperoxide formation of verruculogen in Aspergillus fumigatus</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>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 alpha-ketoglutarate-dependent dioxygenase FtmOx1 from Aspergillus fumigatus, which catalyses the conversion of fumitremorgin B to verruculogen by inserting an endoperoxide bond between two prenyl moieties. Incubation with (18)O(2)-enriched atmosphere demonstrated that both oxygen atoms of the endoperoxide bond are derived from one molecule of O(2). FtmOx1 is the first endoperoxide-forming non-heme Fe(ii) and alpha-ketoglutarate-dependent dioxygenase reported so far. A mechanism of FtmOx1-catalysed verruculogen formation is postulated and discussed.</description><subject>Aspergillus fumigatus - enzymology</subject><subject>Biocatalysis</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Dioxygenases - chemistry</subject><subject>Dioxygenases - metabolism</subject><subject>Heme</subject><subject>Indoles - chemistry</subject><subject>Indoles - metabolism</subject><subject>Iron - metabolism</subject><subject>Ketoglutaric Acids - metabolism</subject><subject>Peroxides - chemistry</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkc1OGzEUhS1UBDQg9Qkq75pKTPEfmfESoaaNhJRNWY9uxtfJFI899Q9KXqTP20GEsjpXOt89i3MI-cTZN86kvtlo1kgtdifkgqu6rtit1B_-34Kdk48p_WaM63qhzsj5i0rJby_I32Ue1nt-TYH64KsdDkiXOF-tvlLwhoIbd1A9YQ5bVzJEyFgZHNEb9JmaPuwPW_SQ8Jp2kMEdEiaad0gnIowYw743SG2IA-Q-eBosfcYYS1dcmB5p7-ldmrht71xJ1Jah30Iu6ZKcWnAJr446I4_L77_uf1YP6x-r-7uHqhONyBU20BkrLYJWZmEaw1B12oLYKGFqxWQtxGTImm1q1oHBhW0EZyiV4VpIJmfky2vuGMOfgim3Q586dA48hpLaWiqmtNaLiZy_kl0MKUW07Rj7AeKh5ax9GaF9G2FCPx9Dy2ZA8w4eW5f_AF6xhMk</recordid><startdate>20090101</startdate><enddate>20090101</enddate><creator>Steffan, Nicola</creator><creator>Grundmann, Alexander</creator><creator>Afiyatullov, Shamil</creator><creator>Ruan, Hanli</creator><creator>Li, Shu-Ming</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20090101</creationdate><title>FtmOx1, a non-heme Fe(II) and alpha-ketoglutarate-dependent dioxygenase, catalyses the endoperoxide formation of verruculogen in Aspergillus fumigatus</title><author>Steffan, Nicola ; Grundmann, Alexander ; Afiyatullov, Shamil ; Ruan, Hanli ; Li, Shu-Ming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c282t-e8acdf3fea94d6d8d0e4c9fa2b42d74037224d6370b70cade6f8210e34d192303</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Aspergillus fumigatus - enzymology</topic><topic>Biocatalysis</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Dioxygenases - chemistry</topic><topic>Dioxygenases - metabolism</topic><topic>Heme</topic><topic>Indoles - chemistry</topic><topic>Indoles - metabolism</topic><topic>Iron - metabolism</topic><topic>Ketoglutaric Acids - metabolism</topic><topic>Peroxides - chemistry</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Steffan, Nicola</creatorcontrib><creatorcontrib>Grundmann, Alexander</creatorcontrib><creatorcontrib>Afiyatullov, Shamil</creatorcontrib><creatorcontrib>Ruan, Hanli</creatorcontrib><creatorcontrib>Li, Shu-Ming</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Steffan, Nicola</au><au>Grundmann, Alexander</au><au>Afiyatullov, Shamil</au><au>Ruan, Hanli</au><au>Li, Shu-Ming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>FtmOx1, a non-heme Fe(II) and alpha-ketoglutarate-dependent dioxygenase, catalyses the endoperoxide formation of verruculogen in Aspergillus fumigatus</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2009-01-01</date><risdate>2009</risdate><volume>7</volume><issue>19</issue><spage>4082</spage><epage>4087</epage><pages>4082-4087</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><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 alpha-ketoglutarate-dependent dioxygenase FtmOx1 from Aspergillus fumigatus, which catalyses the conversion of fumitremorgin B to verruculogen by inserting an endoperoxide bond between two prenyl moieties. Incubation with (18)O(2)-enriched atmosphere demonstrated that both oxygen atoms of the endoperoxide bond are derived from one molecule of O(2). FtmOx1 is the first endoperoxide-forming non-heme Fe(ii) and alpha-ketoglutarate-dependent dioxygenase reported so far. A mechanism of FtmOx1-catalysed verruculogen formation is postulated and discussed.</abstract><cop>England</cop><pmid>19763315</pmid><doi>10.1039/b908392h</doi><tpages>6</tpages></addata></record> |
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| ispartof | Organic & biomolecular chemistry, 2009-01, Vol.7 (19), p.4082-4087 |
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| source | MEDLINE; Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Aspergillus fumigatus - enzymology Biocatalysis Chromatography, High Pressure Liquid Dioxygenases - chemistry Dioxygenases - metabolism Heme Indoles - chemistry Indoles - metabolism Iron - metabolism Ketoglutaric Acids - metabolism Peroxides - chemistry Spectrometry, Mass, Electrospray Ionization |
| title | FtmOx1, a non-heme Fe(II) and alpha-ketoglutarate-dependent dioxygenase, catalyses the endoperoxide formation of verruculogen in Aspergillus fumigatus |
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