Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by 13C,13C COSY NMR Spectroscopy

Kurzanzeige
dc.contributor.authorBarra, Lena
dc.contributor.authorIbrom, Kerstin
dc.contributor.authorDickschat, Jeroen S.
dc.date.accessioned2022-05-23T08:12:43Z
dc.date.available2022-05-23T08:12:43Z
dc.date.issued2015-05-26eng
dc.description.abstractFeeding of (2,3,4,5,6-13C5)mevalonolactone to the fungus Hypomyces odoratus resulted in a completely labeled sesquiterpene ether. The connectivity of the carbon atoms was easily deduced from a 13C,13C COSY spectrum, revealing a structure that was different from the previously reported structure of hypodoratoxide, even though the reported 13C NMR data matched. A structural revision of hypodoratoxide is thus presented. Its absolute configuration was tentatively assigned from its co-metabolite cis-dihydroagarofuran. Its biosynthesis was investigated by feeding of (3-13C)- and (4,6-13C2)mevalonolactone, which gave insights into the complex rearrangement of the carbon skeleton during terpene cyclization by analysis of the 13C,13C couplings.eng
dc.description.versionpublishedeng
dc.identifier.doi10.1002/anie.201501765eng
dc.identifier.pmid25876559eng
dc.identifier.ppn1841631590
dc.identifier.urihttps://kops.uni-konstanz.de/handle/123456789/57617
dc.language.isoengeng
dc.rightsterms-of-use
dc.rights.urihttps://rightsstatements.org/page/InC/1.0/
dc.subject.ddc540eng
dc.titleStructural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by <sup>13</sup>C,<sup>13</sup>C COSY NMR Spectroscopyeng
dc.typeJOURNAL_ARTICLEeng
dspace.entity.typePublication
kops.citation.bibtex
@article{Barra2015-05-26Struc-57617,
  year={2015},
  doi={10.1002/anie.201501765},
  title={Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by <sup>13</sup>C,<sup>13</sup>C COSY NMR Spectroscopy},
  number={22},
  volume={54},
  issn={1433-7851},
  journal={Angewandte Chemie International Edition},
  pages={6637--6640},
  author={Barra, Lena and Ibrom, Kerstin and Dickschat, Jeroen S.}
}
kops.citation.iso690BARRA, Lena, Kerstin IBROM, Jeroen S. DICKSCHAT, 2015. Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by 13C,13C COSY NMR Spectroscopy. In: Angewandte Chemie International Edition. Wiley-Blackwell. 2015, 54(22), pp. 6637-6640. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201501765deu
kops.citation.iso690BARRA, Lena, Kerstin IBROM, Jeroen S. DICKSCHAT, 2015. Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by 13C,13C COSY NMR Spectroscopy. In: Angewandte Chemie International Edition. Wiley-Blackwell. 2015, 54(22), pp. 6637-6640. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201501765eng
kops.citation.rdf
<rdf:RDF
    xmlns:dcterms="http://purl.org/dc/terms/"
    xmlns:dc="http://purl.org/dc/elements/1.1/"
    xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#"
    xmlns:bibo="http://purl.org/ontology/bibo/"
    xmlns:dspace="http://digital-repositories.org/ontologies/dspace/0.1.0#"
    xmlns:foaf="http://xmlns.com/foaf/0.1/"
    xmlns:void="http://rdfs.org/ns/void#"
    xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > 
  <rdf:Description rdf:about="https://kops.uni-konstanz.de/server/rdf/resource/123456789/57617">
    <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2022-05-23T08:12:43Z</dc:date>
    <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2022-05-23T08:12:43Z</dcterms:available>
    <dc:rights>terms-of-use</dc:rights>
    <dcterms:abstract xml:lang="eng">Feeding of (2,3,4,5,6-&lt;sup&gt;13&lt;/sup&gt;C&lt;sub&gt;5&lt;/sub&gt;)mevalonolactone to the fungus Hypomyces odoratus resulted in a completely labeled sesquiterpene ether. The connectivity of the carbon atoms was easily deduced from a &lt;sup&gt;13&lt;/sup&gt;C,&lt;sup&gt;13&lt;/sup&gt;C COSY spectrum, revealing a structure that was different from the previously reported structure of hypodoratoxide, even though the reported 13C NMR data matched. A structural revision of hypodoratoxide is thus presented. Its absolute configuration was tentatively assigned from its co-metabolite cis-dihydroagarofuran. Its biosynthesis was investigated by feeding of (3-&lt;sup&gt;13&lt;/sup&gt;C)- and (4,6-&lt;sup&gt;13&lt;/sup&gt;C&lt;sub&gt;2&lt;/sub&gt;)mevalonolactone, which gave insights into the complex rearrangement of the carbon skeleton during terpene cyclization by analysis of the &lt;sup&gt;13&lt;/sup&gt;C,&lt;sup&gt;13&lt;/sup&gt;C couplings.</dcterms:abstract>
    <dc:language>eng</dc:language>
    <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/>
    <dc:contributor>Barra, Lena</dc:contributor>
    <dc:contributor>Dickschat, Jeroen S.</dc:contributor>
    <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dcterms:rights rdf:resource="https://rightsstatements.org/page/InC/1.0/"/>
    <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/57617/1/Barra_2-ay6vb30e97pr2.pdf"/>
    <foaf:homepage rdf:resource="http://localhost:8080/"/>
    <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dc:creator>Dickschat, Jeroen S.</dc:creator>
    <bibo:uri rdf:resource="https://kops.uni-konstanz.de/handle/123456789/57617"/>
    <dcterms:issued>2015-05-26</dcterms:issued>
    <dc:creator>Ibrom, Kerstin</dc:creator>
    <dc:creator>Barra, Lena</dc:creator>
    <dc:contributor>Ibrom, Kerstin</dc:contributor>
    <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/57617/1/Barra_2-ay6vb30e97pr2.pdf"/>
    <dcterms:title>Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by &lt;sup&gt;13&lt;/sup&gt;C,&lt;sup&gt;13&lt;/sup&gt;C COSY NMR Spectroscopy</dcterms:title>
  </rdf:Description>
</rdf:RDF>
kops.description.openAccessopenaccessgreen
kops.flag.isPeerReviewedtrueeng
kops.flag.knbibliographyfalse
kops.identifier.nbnurn:nbn:de:bsz:352-2-ay6vb30e97pr2
kops.sourcefieldAngewandte Chemie International Edition. Wiley-Blackwell. 2015, <b>54</b>(22), pp. 6637-6640. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201501765deu
kops.sourcefield.plainAngewandte Chemie International Edition. Wiley-Blackwell. 2015, 54(22), pp. 6637-6640. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201501765deu
kops.sourcefield.plainAngewandte Chemie International Edition. Wiley-Blackwell. 2015, 54(22), pp. 6637-6640. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201501765eng
relation.isAuthorOfPublication8af73ca8-4011-4906-89f2-1bce73dadba1
relation.isAuthorOfPublication.latestForDiscovery8af73ca8-4011-4906-89f2-1bce73dadba1
source.bibliographicInfo.fromPage6637eng
source.bibliographicInfo.issue22eng
source.bibliographicInfo.toPage6640eng
source.bibliographicInfo.volume54eng
source.identifier.eissn1521-3773eng
source.identifier.issn1433-7851eng
source.periodicalTitleAngewandte Chemie International Editioneng
source.publisherWiley-Blackwelleng

Dateien

Originalbündel

Gerade angezeigt 1 - 1 von 1
Vorschaubild nicht verfügbar
Name:
Barra_2-ay6vb30e97pr2.pdf
Größe:
174.22 KB
Format:
Adobe Portable Document Format
Barra_2-ay6vb30e97pr2.pdf
Barra_2-ay6vb30e97pr2.pdfGröße: 174.22 KBDownloads: 103

Sammlungen

Chemie: Publikationen