A new enzyme involved in the control of the stereochemistry in the decalin formation during equisetin biosynthesis
Tetramic acid containing a decalin ring such as equisetin and phomasetin is one of the characteristic scaffolds found in fungal bioactive secondary metabolites. Polyketide (PKS)-nonribosomal peptide synthetase (NRPS) hybrid enzyme is responsible for the synthesis of the polyketide scaffold conjugate...
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| Veröffentlicht in: | Biochemical and biophysical research communications 2015-05, Vol.460 (2), p.210-215 |
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| creator | Kato, Naoki Nogawa, Toshihiko Hirota, Hiroshi Jang, Jae-Hyuk Takahashi, Shunji Ahn, Jong Seog Osada, Hiroyuki |
| description | Tetramic acid containing a decalin ring such as equisetin and phomasetin is one of the characteristic scaffolds found in fungal bioactive secondary metabolites. Polyketide (PKS)-nonribosomal peptide synthetase (NRPS) hybrid enzyme is responsible for the synthesis of the polyketide scaffold conjugated with an amino acid. PKS-NRPS hybrid complex programs to create structural diversity in the polyketide backbone have begun to be investigated, yet mechanism of control of the stereochemistry in a decalin formation via a Diels-Alder cycloaddition remains uncertain. Here, we demonstrate that fsa2, which showed no homology to genes encoding proteins of known function, in the fsa cluster responsible for equisetin and fusarisetin A biosynthesis in Fusarium sp. FN080326, is involved in the control of stereochemistry in decalin formation via a Diels-Alder reaction in the equisetin biosynthetic pathway.
•Fusarisetin A biosynthetic gene cluster was identified in Fusarium sp. FN080326.•Equisetin is a biosynthetic intermediate of fusarisetin A.•(3S,6R)-diastereomer of equisetin was isolated from the fsa2 deletion mutant.•Fsa2 is involved in the stereoselective decalin formation of equisetin. |
| doi_str_mv | 10.1016/j.bbrc.2015.03.011 |
| format | Article |
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•Fusarisetin A biosynthetic gene cluster was identified in Fusarium sp. FN080326.•Equisetin is a biosynthetic intermediate of fusarisetin A.•(3S,6R)-diastereomer of equisetin was isolated from the fsa2 deletion mutant.•Fsa2 is involved in the stereoselective decalin formation of equisetin.</description><identifier>ISSN: 0006-291X</identifier><identifier>EISSN: 1090-2104</identifier><identifier>DOI: 10.1016/j.bbrc.2015.03.011</identifier><identifier>PMID: 25770422</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Biosynthesis ; Decalin ; Diels-Alder cycloaddition ; Fusarium - enzymology ; Fusarium - genetics ; Fusarium - metabolism ; Fusarium PKS-NRPS hybrid ; Genes, Fungal ; Multigene Family ; Naphthalenes - metabolism ; Polyketide Synthases - metabolism ; Pyrrolidinones - metabolism ; Secondary metabolite ; Stereoisomerism ; Tetrahydronaphthalenes - metabolism</subject><ispartof>Biochemical and biophysical research communications, 2015-05, Vol.460 (2), p.210-215</ispartof><rights>2015 Elsevier Inc.</rights><rights>Copyright © 2015 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c492t-a562ee56fdaad85a1a71c5379da70a2e65bee5158148b7551ca26ffe838f37a43</citedby><cites>FETCH-LOGICAL-c492t-a562ee56fdaad85a1a71c5379da70a2e65bee5158148b7551ca26ffe838f37a43</cites><orcidid>0000-0002-6600-9775</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0006291X15004362$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25770422$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kato, Naoki</creatorcontrib><creatorcontrib>Nogawa, Toshihiko</creatorcontrib><creatorcontrib>Hirota, Hiroshi</creatorcontrib><creatorcontrib>Jang, Jae-Hyuk</creatorcontrib><creatorcontrib>Takahashi, Shunji</creatorcontrib><creatorcontrib>Ahn, Jong Seog</creatorcontrib><creatorcontrib>Osada, Hiroyuki</creatorcontrib><title>A new enzyme involved in the control of the stereochemistry in the decalin formation during equisetin biosynthesis</title><title>Biochemical and biophysical research communications</title><addtitle>Biochem Biophys Res Commun</addtitle><description>Tetramic acid containing a decalin ring such as equisetin and phomasetin is one of the characteristic scaffolds found in fungal bioactive secondary metabolites. Polyketide (PKS)-nonribosomal peptide synthetase (NRPS) hybrid enzyme is responsible for the synthesis of the polyketide scaffold conjugated with an amino acid. PKS-NRPS hybrid complex programs to create structural diversity in the polyketide backbone have begun to be investigated, yet mechanism of control of the stereochemistry in a decalin formation via a Diels-Alder cycloaddition remains uncertain. Here, we demonstrate that fsa2, which showed no homology to genes encoding proteins of known function, in the fsa cluster responsible for equisetin and fusarisetin A biosynthesis in Fusarium sp. FN080326, is involved in the control of stereochemistry in decalin formation via a Diels-Alder reaction in the equisetin biosynthetic pathway.
•Fusarisetin A biosynthetic gene cluster was identified in Fusarium sp. FN080326.•Equisetin is a biosynthetic intermediate of fusarisetin A.•(3S,6R)-diastereomer of equisetin was isolated from the fsa2 deletion mutant.•Fsa2 is involved in the stereoselective decalin formation of equisetin.</description><subject>Biosynthesis</subject><subject>Decalin</subject><subject>Diels-Alder cycloaddition</subject><subject>Fusarium - enzymology</subject><subject>Fusarium - genetics</subject><subject>Fusarium - metabolism</subject><subject>Fusarium PKS-NRPS hybrid</subject><subject>Genes, Fungal</subject><subject>Multigene Family</subject><subject>Naphthalenes - metabolism</subject><subject>Polyketide Synthases - metabolism</subject><subject>Pyrrolidinones - metabolism</subject><subject>Secondary metabolite</subject><subject>Stereoisomerism</subject><subject>Tetrahydronaphthalenes - metabolism</subject><issn>0006-291X</issn><issn>1090-2104</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1LxDAQhoMouq7-AQ_So5fWJG3SFryI-AWCFwVvIU2mmqVNNElX1l9v1l09CoFMmGdeJg9CJwQXBBN-vii6zquCYsIKXBaYkB00I7jFOSW42kUzjDHPaUteDtBhCAuciIq3--iAsrrGFaUz5C8zC58Z2K_VCJmxSzcsQacii2-QKWejd0Pm-p9niODBqTcYTYh-9UtpUHJIde_8KKNxNtOTN_Y1g4_JBIip1RkXVjbBwYQjtNfLIcDx9p6j55vrp6u7_OHx9v7q8iFXVUtjLhmnAIz3WkrdMElkTRQr61bLGksKnHWpTVhDqqarGSNKUt730JRNX9ayKufobJP77t3HBCGKtLaCYZAW3BQE4TUvy2Z95ohuUOVdCB568e7NKP1KECzWrsVCrF2LtWuBS5FMpqHTbf7UjaD_Rn7lJuBiA0D65dKAF0EZsAq08aCi0M78l_8NOYiSXw</recordid><startdate>20150501</startdate><enddate>20150501</enddate><creator>Kato, Naoki</creator><creator>Nogawa, Toshihiko</creator><creator>Hirota, Hiroshi</creator><creator>Jang, Jae-Hyuk</creator><creator>Takahashi, Shunji</creator><creator>Ahn, Jong Seog</creator><creator>Osada, Hiroyuki</creator><general>Elsevier Inc</general><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><orcidid>https://orcid.org/0000-0002-6600-9775</orcidid></search><sort><creationdate>20150501</creationdate><title>A new enzyme involved in the control of the stereochemistry in the decalin formation during equisetin biosynthesis</title><author>Kato, Naoki ; Nogawa, Toshihiko ; Hirota, Hiroshi ; Jang, Jae-Hyuk ; Takahashi, Shunji ; Ahn, Jong Seog ; Osada, Hiroyuki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c492t-a562ee56fdaad85a1a71c5379da70a2e65bee5158148b7551ca26ffe838f37a43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Biosynthesis</topic><topic>Decalin</topic><topic>Diels-Alder cycloaddition</topic><topic>Fusarium - enzymology</topic><topic>Fusarium - genetics</topic><topic>Fusarium - metabolism</topic><topic>Fusarium PKS-NRPS hybrid</topic><topic>Genes, Fungal</topic><topic>Multigene Family</topic><topic>Naphthalenes - metabolism</topic><topic>Polyketide Synthases - metabolism</topic><topic>Pyrrolidinones - metabolism</topic><topic>Secondary metabolite</topic><topic>Stereoisomerism</topic><topic>Tetrahydronaphthalenes - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kato, Naoki</creatorcontrib><creatorcontrib>Nogawa, Toshihiko</creatorcontrib><creatorcontrib>Hirota, Hiroshi</creatorcontrib><creatorcontrib>Jang, Jae-Hyuk</creatorcontrib><creatorcontrib>Takahashi, Shunji</creatorcontrib><creatorcontrib>Ahn, Jong Seog</creatorcontrib><creatorcontrib>Osada, Hiroyuki</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>Biochemical and biophysical research communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kato, Naoki</au><au>Nogawa, Toshihiko</au><au>Hirota, Hiroshi</au><au>Jang, Jae-Hyuk</au><au>Takahashi, Shunji</au><au>Ahn, Jong Seog</au><au>Osada, Hiroyuki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A new enzyme involved in the control of the stereochemistry in the decalin formation during equisetin biosynthesis</atitle><jtitle>Biochemical and biophysical research communications</jtitle><addtitle>Biochem Biophys Res Commun</addtitle><date>2015-05-01</date><risdate>2015</risdate><volume>460</volume><issue>2</issue><spage>210</spage><epage>215</epage><pages>210-215</pages><issn>0006-291X</issn><eissn>1090-2104</eissn><abstract>Tetramic acid containing a decalin ring such as equisetin and phomasetin is one of the characteristic scaffolds found in fungal bioactive secondary metabolites. Polyketide (PKS)-nonribosomal peptide synthetase (NRPS) hybrid enzyme is responsible for the synthesis of the polyketide scaffold conjugated with an amino acid. PKS-NRPS hybrid complex programs to create structural diversity in the polyketide backbone have begun to be investigated, yet mechanism of control of the stereochemistry in a decalin formation via a Diels-Alder cycloaddition remains uncertain. Here, we demonstrate that fsa2, which showed no homology to genes encoding proteins of known function, in the fsa cluster responsible for equisetin and fusarisetin A biosynthesis in Fusarium sp. FN080326, is involved in the control of stereochemistry in decalin formation via a Diels-Alder reaction in the equisetin biosynthetic pathway.
•Fusarisetin A biosynthetic gene cluster was identified in Fusarium sp. FN080326.•Equisetin is a biosynthetic intermediate of fusarisetin A.•(3S,6R)-diastereomer of equisetin was isolated from the fsa2 deletion mutant.•Fsa2 is involved in the stereoselective decalin formation of equisetin.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>25770422</pmid><doi>10.1016/j.bbrc.2015.03.011</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-6600-9775</orcidid></addata></record> |
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| subjects | Biosynthesis Decalin Diels-Alder cycloaddition Fusarium - enzymology Fusarium - genetics Fusarium - metabolism Fusarium PKS-NRPS hybrid Genes, Fungal Multigene Family Naphthalenes - metabolism Polyketide Synthases - metabolism Pyrrolidinones - metabolism Secondary metabolite Stereoisomerism Tetrahydronaphthalenes - metabolism |
| title | A new enzyme involved in the control of the stereochemistry in the decalin formation during equisetin biosynthesis |
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