Regio- and Stereoselective Oxidative Phenol Coupling in Aspergillus niger
Piecing it together: Aspergillus niger produces kotanin (see structure) by dimerization of the monomeric, polyketide‐synthase‐derived (PKS) 7‐demethylsiderin. A combined approach, comprising bioinformatics and gene‐deletion experiments, identified the biosynthetic cluster responsible for kotanin pro...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2012-09, Vol.51 (39), p.9788-9791 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Gil Girol, Christian Fisch, Katja M. Heinekamp, Thorsten Günther, Stefan Hüttel, Wolfgang Piel, Jörn Brakhage, Axel A. Müller, Michael |
| description | Piecing it together: Aspergillus niger produces kotanin (see structure) by dimerization of the monomeric, polyketide‐synthase‐derived (PKS) 7‐demethylsiderin. A combined approach, comprising bioinformatics and gene‐deletion experiments, identified the biosynthetic cluster responsible for kotanin production. Homology modeling and substrate docking provide a rationale for the regio‐ and stereoselective phenol coupling reaction. |
| doi_str_mv | 10.1002/anie.201203603 |
| format | Article |
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A combined approach, comprising bioinformatics and gene‐deletion experiments, identified the biosynthetic cluster responsible for kotanin production. 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KGaA, Weinheim</rights><rights>Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5433-6c4225477e888e64d43cb275ac839c8ca26cae2e2986cd962a40fe6b73cfa17e3</citedby><cites>FETCH-LOGICAL-c5433-6c4225477e888e64d43cb275ac839c8ca26cae2e2986cd962a40fe6b73cfa17e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201203603$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201203603$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22945023$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gil Girol, Christian</creatorcontrib><creatorcontrib>Fisch, Katja M.</creatorcontrib><creatorcontrib>Heinekamp, Thorsten</creatorcontrib><creatorcontrib>Günther, Stefan</creatorcontrib><creatorcontrib>Hüttel, Wolfgang</creatorcontrib><creatorcontrib>Piel, Jörn</creatorcontrib><creatorcontrib>Brakhage, Axel A.</creatorcontrib><creatorcontrib>Müller, Michael</creatorcontrib><title>Regio- and Stereoselective Oxidative Phenol Coupling in Aspergillus niger</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>Piecing it together: Aspergillus niger produces kotanin (see structure) by dimerization of the monomeric, polyketide‐synthase‐derived (PKS) 7‐demethylsiderin. A combined approach, comprising bioinformatics and gene‐deletion experiments, identified the biosynthetic cluster responsible for kotanin production. Homology modeling and substrate docking provide a rationale for the regio‐ and stereoselective phenol coupling reaction.</description><subject>Aspergillus niger</subject><subject>Aspergillus niger - chemistry</subject><subject>Aspergillus niger - enzymology</subject><subject>Aspergillus niger - metabolism</subject><subject>biaryls</subject><subject>Bioinformatics</subject><subject>biosynthesis</subject><subject>Clusters</subject><subject>Coumarins - chemistry</subject><subject>Coumarins - metabolism</subject><subject>CC coupling</subject><subject>Dimerization</subject><subject>Docking</subject><subject>Homology</subject><subject>Joining</subject><subject>Models, Molecular</subject><subject>natural products</subject><subject>Oxidative Coupling</subject><subject>Phenol</subject><subject>Phenols - chemistry</subject><subject>Phenols - metabolism</subject><subject>polyketides</subject><subject>Polyketides - chemistry</subject><subject>Polyketides - metabolism</subject><subject>Stereoisomerism</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU1vEzEQhi1ERT_gyhGtxIXLBtuz_jpGUWkjSosKCImL5XgnwcXZDXYW2n-PQ9qo6iUnz-F5H43nJeQ1oyNGKX_vuoAjThmnICk8I0dMcFaDUvC8zA1ArbRgh-Q455vCa03lC3LIuWkE5XBEpte4CH1dua6tvqwxYZ8xol-HP1hd3YbW_Z8-_8Suj9WkH1YxdIsqdNU4rzAtQoxDrrqwwPSSHMxdzPjq_j0h3z6cfp2c1xdXZ9PJ-KL2YrOO9A3nolEKtdYom7YBP-NKOK_BeO0dl94hR2609K2R3DV0jnKmwM8dUwgn5N3Wu0r97wHz2i5D9hij67AfsmWKMsaMMXQ_KsrZlAGj9qO0YcDB6I317RP0ph9SV_5chEwqyiWwQo22lE99zgnndpXC0qW7orKb6uymOrurrgTe3GuH2RLbHf7QVQHMFvgbIt7t0dnx5fT0sbzeZkNe4-0u69IvKxUoYb9fntkfGiZafPpor-EfmFSx5Q</recordid><startdate>20120924</startdate><enddate>20120924</enddate><creator>Gil Girol, Christian</creator><creator>Fisch, Katja M.</creator><creator>Heinekamp, Thorsten</creator><creator>Günther, Stefan</creator><creator>Hüttel, Wolfgang</creator><creator>Piel, Jörn</creator><creator>Brakhage, Axel A.</creator><creator>Müller, Michael</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>M7N</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20120924</creationdate><title>Regio- and Stereoselective Oxidative Phenol Coupling in Aspergillus niger</title><author>Gil Girol, Christian ; Fisch, Katja M. ; Heinekamp, Thorsten ; Günther, Stefan ; Hüttel, Wolfgang ; Piel, Jörn ; Brakhage, Axel A. ; Müller, Michael</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5433-6c4225477e888e64d43cb275ac839c8ca26cae2e2986cd962a40fe6b73cfa17e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Aspergillus niger</topic><topic>Aspergillus niger - chemistry</topic><topic>Aspergillus niger - enzymology</topic><topic>Aspergillus niger - metabolism</topic><topic>biaryls</topic><topic>Bioinformatics</topic><topic>biosynthesis</topic><topic>Clusters</topic><topic>Coumarins - chemistry</topic><topic>Coumarins - metabolism</topic><topic>CC coupling</topic><topic>Dimerization</topic><topic>Docking</topic><topic>Homology</topic><topic>Joining</topic><topic>Models, Molecular</topic><topic>natural products</topic><topic>Oxidative Coupling</topic><topic>Phenol</topic><topic>Phenols - chemistry</topic><topic>Phenols - metabolism</topic><topic>polyketides</topic><topic>Polyketides - chemistry</topic><topic>Polyketides - metabolism</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gil Girol, Christian</creatorcontrib><creatorcontrib>Fisch, Katja M.</creatorcontrib><creatorcontrib>Heinekamp, Thorsten</creatorcontrib><creatorcontrib>Günther, Stefan</creatorcontrib><creatorcontrib>Hüttel, Wolfgang</creatorcontrib><creatorcontrib>Piel, Jörn</creatorcontrib><creatorcontrib>Brakhage, Axel A.</creatorcontrib><creatorcontrib>Müller, Michael</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gil Girol, Christian</au><au>Fisch, Katja M.</au><au>Heinekamp, Thorsten</au><au>Günther, Stefan</au><au>Hüttel, Wolfgang</au><au>Piel, Jörn</au><au>Brakhage, Axel A.</au><au>Müller, Michael</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regio- and Stereoselective Oxidative Phenol Coupling in Aspergillus niger</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2012-09-24</date><risdate>2012</risdate><volume>51</volume><issue>39</issue><spage>9788</spage><epage>9791</epage><pages>9788-9791</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>Piecing it together: Aspergillus niger produces kotanin (see structure) by dimerization of the monomeric, polyketide‐synthase‐derived (PKS) 7‐demethylsiderin. A combined approach, comprising bioinformatics and gene‐deletion experiments, identified the biosynthetic cluster responsible for kotanin production. Homology modeling and substrate docking provide a rationale for the regio‐ and stereoselective phenol coupling reaction.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>22945023</pmid><doi>10.1002/anie.201203603</doi><tpages>4</tpages><edition>International ed. in English</edition></addata></record> |
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| subjects | Aspergillus niger Aspergillus niger - chemistry Aspergillus niger - enzymology Aspergillus niger - metabolism biaryls Bioinformatics biosynthesis Clusters Coumarins - chemistry Coumarins - metabolism CC coupling Dimerization Docking Homology Joining Models, Molecular natural products Oxidative Coupling Phenol Phenols - chemistry Phenols - metabolism polyketides Polyketides - chemistry Polyketides - metabolism Stereoisomerism |
| title | Regio- and Stereoselective Oxidative Phenol Coupling in Aspergillus niger |
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