Identification of Novel α-Pyrones from Conexibacter woesei Serving as Sulfate Shuttles.
Identifieur interne : 000135 ( Main/Exploration ); précédent : 000134; suivant : 000136Identification of Novel α-Pyrones from Conexibacter woesei Serving as Sulfate Shuttles.
Auteurs : Franziska Wiker [Allemagne] ; Martin Konnerth [Allemagne] ; Irina Helmle [Allemagne] ; Andreas Kulik [Allemagne] ; Leonard Kaysser [Allemagne] ; Harald Gross [Allemagne] ; Bertolt Gust [Allemagne]Source :
- ACS chemical biology [ 1554-8937 ] ; 2019.
Descripteurs français
- KwdFr :
- Actinobacteria (composition chimique), Arylsulfotransferase (métabolisme), PAPS (métabolisme), Polyketide synthases (génétique), Protéines bactériennes (génétique), Protéines bactériennes (métabolisme), Pyrones (isolement et purification), Pyrones (métabolisme), Streptomyces coelicolor (génétique), Sulfates organiques (métabolisme).
- MESH :
- composition chimique : Actinobacteria.
- génétique : Polyketide synthases, Protéines bactériennes, Streptomyces coelicolor.
- isolement et purification : Pyrones.
- métabolisme : Arylsulfotransferase, PAPS, Protéines bactériennes, Pyrones, Sulfates organiques.
English descriptors
- KwdEn :
- Actinobacteria (chemistry), Arylsulfotransferase (metabolism), Bacterial Proteins (genetics), Bacterial Proteins (metabolism), Phosphoadenosine Phosphosulfate (metabolism), Polyketide Synthases (genetics), Pyrones (isolation & purification), Pyrones (metabolism), Streptomyces coelicolor (genetics), Sulfuric Acid Esters (metabolism).
- MESH :
- chemical , genetics : Bacterial Proteins, Polyketide Synthases.
- chemical , isolation & purification : Pyrones.
- chemical , metabolism : Arylsulfotransferase, Bacterial Proteins, Phosphoadenosine Phosphosulfate, Pyrones, Sulfuric Acid Esters.
- chemistry : Actinobacteria.
- genetics : Streptomyces coelicolor.
Abstract
Pyrones comprise a structurally diverse class of compounds. Although they are widespread in nature, their specific physiological functions remain unknown in most cases. We recently described that triketide pyrones mediate the sulfotransfer in caprazamycin biosynthesis. Herein, we report the identification of conexipyrones A-C, three previously unrecognized tetra-substituted α-pyrones, from the soil actinobacterium Conexibacter woesei. Insights into their biosynthesis via a type III polyketide synthase were obtained by feeding studies using isotope-enriched precursors. In vitro assays employing the genetically associated 3'-phosphoadenosine-5'-phosphosulfate (PAPS)-dependent sulfotransferase CwoeST revealed conexipyrones as the enzymes' genuine sulfate acceptor substrates. Furthermore, conexipyrones were determined to function as sulfate shuttles in a two-enzyme assay, because their sulfated derivatives were accepted as donor molecules by the PAPS-independent arylsulfate sulfotransferase (ASST) Cpz4 to yield sulfated caprazamycin intermediates.
DOI: 10.1021/acschembio.9b00455
PubMed: 31419109
Affiliations:
Links toward previous steps (curation, corpus...)
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Germany.</nlm:affiliation><country xml:lang="fr">Allemagne</country><wicri:regionArea>German Center for Infection Research (DZIF) , Partner Site Tübingen, 72076 Tübingen </wicri:regionArea><placeName><region type="land" nuts="1">Bade-Wurtemberg</region><region type="district" nuts="2">District de Tübingen</region><settlement type="city">Tübingen</settlement></placeName></affiliation></author></analytic><series><title level="j">ACS chemical biology</title><idno type="eISSN">1554-8937</idno><imprint><date when="2019" type="published">2019</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Actinobacteria (chemistry)</term><term>Arylsulfotransferase (metabolism)</term><term>Bacterial Proteins (genetics)</term><term>Bacterial Proteins (metabolism)</term><term>Phosphoadenosine Phosphosulfate (metabolism)</term><term>Polyketide Synthases (genetics)</term><term>Pyrones (isolation & purification)</term><term>Pyrones (metabolism)</term><term>Streptomyces coelicolor (genetics)</term><term>Sulfuric Acid Esters (metabolism)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Actinobacteria (composition chimique)</term><term>Arylsulfotransferase (métabolisme)</term><term>PAPS (métabolisme)</term><term>Polyketide synthases (génétique)</term><term>Protéines bactériennes (génétique)</term><term>Protéines bactériennes (métabolisme)</term><term>Pyrones (isolement et purification)</term><term>Pyrones (métabolisme)</term><term>Streptomyces coelicolor (génétique)</term><term>Sulfates organiques (métabolisme)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="genetics" xml:lang="en"><term>Bacterial Proteins</term><term>Polyketide Synthases</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Pyrones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Arylsulfotransferase</term><term>Bacterial Proteins</term><term>Phosphoadenosine Phosphosulfate</term><term>Pyrones</term><term>Sulfuric Acid Esters</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Actinobacteria</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Actinobacteria</term></keywords><keywords scheme="MESH" qualifier="genetics" xml:lang="en"><term>Streptomyces coelicolor</term></keywords><keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>Polyketide synthases</term><term>Protéines bactériennes</term><term>Streptomyces coelicolor</term></keywords><keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Pyrones</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Arylsulfotransferase</term><term>PAPS</term><term>Protéines bactériennes</term><term>Pyrones</term><term>Sulfates organiques</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Pyrones comprise a structurally diverse class of compounds. Although they are widespread in nature, their specific physiological functions remain unknown in most cases. We recently described that triketide pyrones mediate the sulfotransfer in caprazamycin biosynthesis. Herein, we report the identification of conexipyrones A-C, three previously unrecognized tetra-substituted α-pyrones, from the soil actinobacterium <i>Conexibacter woesei</i>. Insights into their biosynthesis via a type III polyketide synthase were obtained by feeding studies using isotope-enriched precursors. <i>In vitro</i> assays employing the genetically associated 3'-phosphoadenosine-5'-phosphosulfate (PAPS)-dependent sulfotransferase CwoeST revealed conexipyrones as the enzymes' genuine sulfate acceptor substrates. Furthermore, conexipyrones were determined to function as sulfate shuttles in a two-enzyme assay, because their sulfated derivatives were accepted as donor molecules by the PAPS-independent arylsulfate sulfotransferase (ASST) Cpz4 to yield sulfated caprazamycin intermediates.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">31419109</PMID><DateCompleted><Year>2020</Year><Month>04</Month><Day>06</Day></DateCompleted><DateRevised><Year>2020</Year><Month>04</Month><Day>08</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1554-8937</ISSN><JournalIssue CitedMedium="Internet"><Volume>14</Volume><Issue>9</Issue><PubDate><Year>2019</Year><Month>09</Month><Day>20</Day></PubDate></JournalIssue><Title>ACS chemical biology</Title><ISOAbbreviation>ACS Chem Biol</ISOAbbreviation></Journal><ArticleTitle>Identification of Novel α-Pyrones from <i>Conexibacter woesei</i> Serving as Sulfate Shuttles.</ArticleTitle><Pagination><MedlinePgn>1972-1980</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/acschembio.9b00455</ELocationID><Abstract><AbstractText>Pyrones comprise a structurally diverse class of compounds. Although they are widespread in nature, their specific physiological functions remain unknown in most cases. We recently described that triketide pyrones mediate the sulfotransfer in caprazamycin biosynthesis. Herein, we report the identification of conexipyrones A-C, three previously unrecognized tetra-substituted α-pyrones, from the soil actinobacterium <i>Conexibacter woesei</i>. Insights into their biosynthesis via a type III polyketide synthase were obtained by feeding studies using isotope-enriched precursors. <i>In vitro</i> assays employing the genetically associated 3'-phosphoadenosine-5'-phosphosulfate (PAPS)-dependent sulfotransferase CwoeST revealed conexipyrones as the enzymes' genuine sulfate acceptor substrates. Furthermore, conexipyrones were determined to function as sulfate shuttles in a two-enzyme assay, because their sulfated derivatives were accepted as donor molecules by the PAPS-independent arylsulfate sulfotransferase (ASST) Cpz4 to yield sulfated caprazamycin intermediates.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Wiker</LastName><ForeName>Franziska</ForeName><Initials>F</Initials><AffiliationInfo><Affiliation>Pharmaceutical Institute, Department of Pharmaceutical Biology , University of Tübingen , Auf der Morgenstelle 8 , 72076 Tübingen , Germany.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Konnerth</LastName><ForeName>Martin</ForeName><Initials>M</Initials><Identifier Source="ORCID">0000-0002-2988-989X</Identifier><AffiliationInfo><Affiliation>Organic Chemistry , University of Tübingen , Auf der Morgenstelle 18 , 72076 Tübingen , Germany.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Helmle</LastName><ForeName>Irina</ForeName><Initials>I</Initials><AffiliationInfo><Affiliation>Pharmaceutical Institute, Department of Pharmaceutical Biology , University of Tübingen , Auf der Morgenstelle 8 , 72076 Tübingen , Germany.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kulik</LastName><ForeName>Andreas</ForeName><Initials>A</Initials><Identifier Source="ORCID">0000-0002-6914-7313</Identifier><AffiliationInfo><Affiliation>Institute of Microbiology and Infection Medicine , Auf der Morgenstelle 28 , 72076 Tübingen , Germany.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kaysser</LastName><ForeName>Leonard</ForeName><Initials>L</Initials><Identifier Source="ORCID">0000-0002-3943-993X</Identifier><AffiliationInfo><Affiliation>Pharmaceutical Institute, Department of Pharmaceutical Biology , University of Tübingen , Auf der Morgenstelle 8 , 72076 Tübingen , Germany.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>German Center for Infection Research (DZIF) , Partner Site Tübingen, 72076 Tübingen , Germany.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Gross</LastName><ForeName>Harald</ForeName><Initials>H</Initials><Identifier Source="ORCID">0000-0002-0731-821X</Identifier><AffiliationInfo><Affiliation>Pharmaceutical Institute, Department of Pharmaceutical Biology , University of Tübingen , Auf der Morgenstelle 8 , 72076 Tübingen , Germany.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>German Center for Infection Research (DZIF) , Partner Site Tübingen, 72076 Tübingen , Germany.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Gust</LastName><ForeName>Bertolt</ForeName><Initials>B</Initials><Identifier Source="ORCID">0000-0002-1265-0065</Identifier><AffiliationInfo><Affiliation>Pharmaceutical Institute, Department of Pharmaceutical Biology , University of Tübingen , Auf der Morgenstelle 8 , 72076 Tübingen , Germany.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>German Center for Infection Research (DZIF) , Partner Site Tübingen, 72076 Tübingen , Germany.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2019</Year><Month>08</Month><Day>27</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>ACS Chem Biol</MedlineTA><NlmUniqueID>101282906</NlmUniqueID><ISSNLinking>1554-8929</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D001426">Bacterial Proteins</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011753">Pyrones</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D013463">Sulfuric Acid Esters</NameOfSubstance></Chemical><Chemical><RegistryNumber>482-67-7</RegistryNumber><NameOfSubstance UI="D010724">Phosphoadenosine Phosphosulfate</NameOfSubstance></Chemical><Chemical><RegistryNumber>79956-01-7</RegistryNumber><NameOfSubstance UI="D048630">Polyketide Synthases</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 2.8.2.1</RegistryNumber><NameOfSubstance UI="D015239">Arylsulfotransferase</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 2.8.2.22</RegistryNumber><NameOfSubstance UI="C090707">arylsulfate sulfotransferase</NameOfSubstance></Chemical></ChemicalList><SupplMeshList><SupplMeshName Type="Organism" UI="C000648565">Conexibacter woesei</SupplMeshName></SupplMeshList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D039903" MajorTopicYN="N">Actinobacteria</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015239" MajorTopicYN="N">Arylsulfotransferase</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001426" MajorTopicYN="N">Bacterial Proteins</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010724" MajorTopicYN="N">Phosphoadenosine Phosphosulfate</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D048630" MajorTopicYN="N">Polyketide Synthases</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011753" MajorTopicYN="N">Pyrones</DescriptorName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D048372" MajorTopicYN="N">Streptomyces coelicolor</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013463" MajorTopicYN="N">Sulfuric Acid Esters</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2019</Year><Month>8</Month><Day>17</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>4</Month><Day>9</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2019</Year><Month>8</Month><Day>17</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">31419109</ArticleId><ArticleId IdType="doi">10.1021/acschembio.9b00455</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Allemagne</li></country><region><li>Bade-Wurtemberg</li><li>District de Tübingen</li></region><settlement><li>Tübingen</li></settlement></list><tree><country name="Allemagne"><region name="Bade-Wurtemberg"><name sortKey="Wiker, Franziska" sort="Wiker, Franziska" uniqKey="Wiker F" first="Franziska" last="Wiker">Franziska Wiker</name></region><name sortKey="Gross, Harald" sort="Gross, Harald" uniqKey="Gross H" first="Harald" last="Gross">Harald Gross</name><name sortKey="Gross, Harald" sort="Gross, Harald" uniqKey="Gross H" first="Harald" last="Gross">Harald Gross</name><name sortKey="Gust, Bertolt" sort="Gust, Bertolt" uniqKey="Gust B" first="Bertolt" last="Gust">Bertolt Gust</name><name sortKey="Gust, Bertolt" sort="Gust, Bertolt" uniqKey="Gust B" first="Bertolt" last="Gust">Bertolt Gust</name><name sortKey="Helmle, Irina" sort="Helmle, Irina" uniqKey="Helmle I" first="Irina" last="Helmle">Irina Helmle</name><name sortKey="Kaysser, Leonard" sort="Kaysser, Leonard" uniqKey="Kaysser L" first="Leonard" last="Kaysser">Leonard Kaysser</name><name sortKey="Kaysser, Leonard" sort="Kaysser, Leonard" uniqKey="Kaysser L" first="Leonard" last="Kaysser">Leonard Kaysser</name><name sortKey="Konnerth, Martin" sort="Konnerth, Martin" uniqKey="Konnerth M" first="Martin" last="Konnerth">Martin Konnerth</name><name sortKey="Kulik, Andreas" sort="Kulik, Andreas" uniqKey="Kulik A" first="Andreas" last="Kulik">Andreas Kulik</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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{{Explor lien
|wiki= Bois
|area= SulfurTransferaseV1
|flux= Main
|étape= Exploration
|type= RBID
|clé= pubmed:31419109
|texte= Identification of Novel α-Pyrones from Conexibacter woesei Serving as Sulfate Shuttles.
}}
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| HfdSelect -Kh $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd \
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