Publikation: A method for investigating the stereochemical course of terpene cyclisations
Lade...
Dateien
Datum
2016
Autor:innen
Herausgeber:innen
ISSN der Zeitschrift
Electronic ISSN
ISBN
Bibliografische Daten
Verlag
Schriftenreihe
Auflagebezeichnung
URI (zitierfähiger Link)
DOI (zitierfähiger Link)
Internationale Patentnummer
Link zur Lizenz
Angaben zur Forschungsförderung
Projekt
Open Access-Veröffentlichung
Open Access Green
Sammlungen
Core Facility der Universität Konstanz
Titel in einer weiteren Sprache
Publikationstyp
Zeitschriftenartikel
Publikationsstatus
Published
Erschienen in
Organic & Biomolecular Chemistry. Royal Society of Chemistry. 2016, 14(1), pp. 158-164. ISSN 1477-0520. eISSN 1477-0539. Available under: doi: 10.1039/c5ob01998b
Zusammenfassung
Three sesquiterpene cyclases from Streptomyces scabei 87.22, Streptomyces venezuelae ATCC 10712 and Streptomyces clavuligerus ATCC 27064 were characterised and their products were identified as (-)-neomeranol B, (+)-isodauc-8-en-11-ol and (+)-intermedeol, respectively. The stereochemical courses of the terpene cyclisations were investigated by use of various (13)C-labelled FPP isotopomers. A quick and easy test was developed that allows to distinguish reprotonations of olefinic double bonds in neutral intermediates from the two stereoheterotopic faces. The method makes use of incubating (13)C-FPP isotopomers labelled at the reprotonated carbon in deuterium oxide and subsequent HSQC analysis of the product. A 1,7-cyclisation towards (+)-isodauc-8-en-11-ol was followed by use of (1,7-(13)C2)FPP. Surprisingly, the (+)-isodauc-8-en-11-ol also accepted (2Z,6E)-FPP resulting in the same product profile as obtained from (2E,6E)-FPP.
Zusammenfassung in einer weiteren Sprache
Fachgebiet (DDC)
540 Chemie
Schlagwörter
Konferenz
Rezension
undefined / . - undefined, undefined
Zitieren
ISO 690
RABE, Patrick, Jan RINKEL, Tim A. KLAPSCHINSKI, Lena BARRA, Jeroen S. DICKSCHAT, 2016. A method for investigating the stereochemical course of terpene cyclisations. In: Organic & Biomolecular Chemistry. Royal Society of Chemistry. 2016, 14(1), pp. 158-164. ISSN 1477-0520. eISSN 1477-0539. Available under: doi: 10.1039/c5ob01998bBibTex
@article{Rabe2016-01-07metho-57621,
year={2016},
doi={10.1039/c5ob01998b},
title={A method for investigating the stereochemical course of terpene cyclisations},
number={1},
volume={14},
issn={1477-0520},
journal={Organic & Biomolecular Chemistry},
pages={158--164},
author={Rabe, Patrick and Rinkel, Jan and Klapschinski, Tim A. and Barra, Lena and Dickschat, Jeroen S.}
}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/123456789/57621">
<dc:creator>Barra, Lena</dc:creator>
<dc:rights>terms-of-use</dc:rights>
<dc:creator>Rinkel, Jan</dc:creator>
<dc:contributor>Dickschat, Jeroen S.</dc:contributor>
<void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/>
<dcterms:title>A method for investigating the stereochemical course of terpene cyclisations</dcterms:title>
<dcterms:rights rdf:resource="https://rightsstatements.org/page/InC/1.0/"/>
<dc:creator>Rabe, Patrick</dc:creator>
<dc:contributor>Rinkel, Jan</dc:contributor>
<foaf:homepage rdf:resource="http://localhost:8080/"/>
<dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
<dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2022-05-23T08:23:16Z</dcterms:available>
<dc:contributor>Klapschinski, Tim A.</dc:contributor>
<bibo:uri rdf:resource="https://kops.uni-konstanz.de/handle/123456789/57621"/>
<dc:creator>Dickschat, Jeroen S.</dc:creator>
<dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/57621/1/Rabe_2-2pe0i2h0h50g7.pdf"/>
<dc:contributor>Barra, Lena</dc:contributor>
<dcterms:issued>2016-01-07</dcterms:issued>
<dc:contributor>Rabe, Patrick</dc:contributor>
<dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2022-05-23T08:23:16Z</dc:date>
<dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/57621/1/Rabe_2-2pe0i2h0h50g7.pdf"/>
<dcterms:abstract xml:lang="eng">Three sesquiterpene cyclases from Streptomyces scabei 87.22, Streptomyces venezuelae ATCC 10712 and Streptomyces clavuligerus ATCC 27064 were characterised and their products were identified as (-)-neomeranol B, (+)-isodauc-8-en-11-ol and (+)-intermedeol, respectively. The stereochemical courses of the terpene cyclisations were investigated by use of various (13)C-labelled FPP isotopomers. A quick and easy test was developed that allows to distinguish reprotonations of olefinic double bonds in neutral intermediates from the two stereoheterotopic faces. The method makes use of incubating (13)C-FPP isotopomers labelled at the reprotonated carbon in deuterium oxide and subsequent HSQC analysis of the product. A 1,7-cyclisation towards (+)-isodauc-8-en-11-ol was followed by use of (1,7-(13)C2)FPP. Surprisingly, the (+)-isodauc-8-en-11-ol also accepted (2Z,6E)-FPP resulting in the same product profile as obtained from (2E,6E)-FPP.</dcterms:abstract>
<dc:creator>Klapschinski, Tim A.</dc:creator>
<dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
<dc:language>eng</dc:language>
</rdf:Description>
</rdf:RDF>Interner Vermerk
xmlui.Submission.submit.DescribeStep.inputForms.label.kops_note_fromSubmitter
Prüfungsdatum der Dissertation
Finanzierungsart
Kommentar zur Publikation
Allianzlizenz
Corresponding Authors der Uni Konstanz vorhanden
Internationale Co-Autor:innen
Universitätsbibliographie
Nein
Begutachtet
Ja
