Publikation: Structural comparison of oligoribonucleotides and their 2 -Deoxy-2 -fluoro analogs by heteronuclear NMR spectroscopy
Dateien
Datum
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
Sammlungen
Core Facility der Universität Konstanz
Titel in einer weiteren Sprache
Publikationstyp
Publikationsstatus
Erschienen in
Zusammenfassung
1-(2-Deoxy-2-fluororibofuranosyl)pyrimidines were synthesized and incorporated into an RNA oligonucleotide to give 5-r[CfGCf(UfUfCfG)GCfG]-3 (Cf: short form of Cd2f2 = 2-deoxy-2-fluorocytidine; Uf: short form of Ud2f2 = 2-deoxy-2-fluorouridine). The oligomer was investigated by means of UV, CD, and NMR spectroscopy to address the question of how F-labels can substitute 13C-labels in the ribose ring. Through-space (NOE) and through-bond (scalar couplings) experiments were performed that make use of the ameliorated chemical-shift dispersion induced by 19F as an alternative heteronucleus. A comparison of the structures of fluorinated vs. unmodified oligomer is given. It turns out that the fluorinated oligonucleotide exists in a 14:3 equilibrium between a hairpin and a duplex conformation, in contrast to the unmodified oligonucleotide which predominantly adopts the hairpin conformation. Furthermore, the fluorinated hairpin structure adopts two distinct conformations that differ in the sugar conformation of the U and C nucleoside units, as detected by the 19F-NMR chemical shifts. The role of the 2-OH group as stabilizing element in RNA secondary structure is discussed.
Zusammenfassung in einer weiteren Sprache
Fachgebiet (DDC)
Schlagwörter
Konferenz
Rezension
Zitieren
ISO 690
REIF, Bernd, Valentin WITTMANN, Harald SCHWALBE, Christian GRIESINGER, Karlheinz WÖRNER, Kerstin JAHN-HOFMANN, Joachim W. ENGELS, Wolfgang BERMEL, 1997. Structural comparison of oligoribonucleotides and their 2 -Deoxy-2 -fluoro analogs by heteronuclear NMR spectroscopy. In: Helvetica Chimica Acta. 1997, 80(6), pp. 1952-1971. ISSN 0018-019X. eISSN 1522-2675. Available under: doi: 10.1002/hlca.19970800614BibTex
@article{Reif1997Struc-9561, year={1997}, doi={10.1002/hlca.19970800614}, title={Structural comparison of oligoribonucleotides and their 2 -Deoxy-2 -fluoro analogs by heteronuclear NMR spectroscopy}, number={6}, volume={80}, issn={0018-019X}, journal={Helvetica Chimica Acta}, pages={1952--1971}, author={Reif, Bernd and Wittmann, Valentin and Schwalbe, Harald and Griesinger, Christian and Wörner, Karlheinz and Jahn-Hofmann, Kerstin and Engels, Joachim W. and Bermel, Wolfgang} }
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/123456789/9561"> <dc:creator>Engels, Joachim W.</dc:creator> <dc:contributor>Griesinger, Christian</dc:contributor> <dcterms:issued>1997</dcterms:issued> <dc:creator>Wörner, Karlheinz</dc:creator> <dcterms:bibliographicCitation>First publ. in: Helvetica Chimica Acta 80 (1997), pp. 1952-1971</dcterms:bibliographicCitation> <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/9561/1/Structural_comparison_of_oligoribonucleotides_and_their.pdf"/> <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T18:12:46Z</dcterms:available> <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T18:12:46Z</dc:date> <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/9561"/> <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/9561/1/Structural_comparison_of_oligoribonucleotides_and_their.pdf"/> <dc:contributor>Bermel, Wolfgang</dc:contributor> <dcterms:abstract xml:lang="eng">1-(2-Deoxy-2-fluororibofuranosyl)pyrimidines were synthesized and incorporated into an RNA oligonucleotide to give 5-r[CfGCf(UfUfCfG)GCfG]-3 (Cf: short form of Cd2f2 = 2-deoxy-2-fluorocytidine; Uf: short form of Ud2f2 = 2-deoxy-2-fluorouridine). The oligomer was investigated by means of UV, CD, and NMR spectroscopy to address the question of how F-labels can substitute 13C-labels in the ribose ring. Through-space (NOE) and through-bond (scalar couplings) experiments were performed that make use of the ameliorated chemical-shift dispersion induced by 19F as an alternative heteronucleus. A comparison of the structures of fluorinated vs. unmodified oligomer is given. It turns out that the fluorinated oligonucleotide exists in a 14:3 equilibrium between a hairpin and a duplex conformation, in contrast to the unmodified oligonucleotide which predominantly adopts the hairpin conformation. Furthermore, the fluorinated hairpin structure adopts two distinct conformations that differ in the sugar conformation of the U and C nucleoside units, as detected by the 19F-NMR chemical shifts. The role of the 2-OH group as stabilizing element in RNA secondary structure is discussed.</dcterms:abstract> <dc:contributor>Engels, Joachim W.</dc:contributor> <dc:rights>Attribution-NonCommercial-NoDerivs 2.0 Generic</dc:rights> <foaf:homepage rdf:resource="http://localhost:8080/"/> <dc:creator>Bermel, Wolfgang</dc:creator> <dc:contributor>Wörner, Karlheinz</dc:contributor> <dc:contributor>Wittmann, Valentin</dc:contributor> <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/> <dc:creator>Jahn-Hofmann, Kerstin</dc:creator> <dc:language>eng</dc:language> <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/> <dc:contributor>Jahn-Hofmann, Kerstin</dc:contributor> <dc:creator>Reif, Bernd</dc:creator> <dc:contributor>Schwalbe, Harald</dc:contributor> <dc:creator>Griesinger, Christian</dc:creator> <dc:format>application/pdf</dc:format> <dcterms:title>Structural comparison of oligoribonucleotides and their 2 -Deoxy-2 -fluoro analogs by heteronuclear NMR spectroscopy</dcterms:title> <dcterms:rights rdf:resource="http://creativecommons.org/licenses/by-nc-nd/2.0/"/> <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/> <dc:creator>Wittmann, Valentin</dc:creator> <dc:contributor>Reif, Bernd</dc:contributor> <dc:creator>Schwalbe, Harald</dc:creator> </rdf:Description> </rdf:RDF>