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Ferrocenyl GNA Nucleosides: A Bridge between Organic and Organometallic Xeno-nucleic Acids

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cris.lastimport.scopus2024-02-12T20:56:01Z
dc.abstract.enThe enantioselective synthesis and electrochemistry of the first ferrocenyl GNA nucleosides is reported. These compounds were obtained by a Sharpless asymmetric dihydroxylation reaction of [3‐(N1‐thyminyl)‐1‐(ferrocenyl)]propene as S,R and R,S enantiomers in about 70 % yield with enantiomeric excesses of >99 % and 71 %, respectively. The absolute configurations of the chiral carbon atoms in the nucleosides were assigned by single‐crystal X‐ray diffraction analysis of the methyl derivatives in the solid state. The compounds were also studied with circular dichroism (CD) spectroscopy in solution. The enantiomeric relationship between the S,R and R,S isomers was confirmed by the near‐mirror‐image CD spectra. The redox properties of the nucleosides and their methylated derivatives were investigated using cyclic voltammetry. The cyclic voltammograms revealed reversible redox processes for the entire series of compounds at potentials of −25 mV (for nonmethylated derivatives) and 75 mV (for methylated derivatives) versus the ferrocene/ferrocenium reference redox couple.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorVrček, Valerije
dc.contributor.authorKowalski, Konrad
dc.contributor.authorGyurcsik, Béla
dc.contributor.authorHildebrandt, Alexander
dc.contributor.authorYuan, Qing
dc.contributor.authorSkiba, Joanna
dc.contributor.authorBalogh, Ria K.
dc.contributor.authorLang, Heinrich
dc.contributor.authorTrzybiński, Damian
dc.contributor.authorWoźniak, Krzysztof
dc.date.accessioned2024-01-25T00:40:03Z
dc.date.available2024-01-25T00:40:03Z
dc.date.issued2018
dc.description.financeNie dotyczy
dc.description.number2
dc.description.volume83
dc.identifier.doi10.1002/CPLU.201700551
dc.identifier.issn2192-6506
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/107070
dc.identifier.weblinkhttps://onlinelibrary.wiley.com/doi/abs/10.1002/cplu.201700551
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofChemPlusChem
dc.relation.pages77-86
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.subject.enbioorganometallic compounds
dc.subject.enferrocene
dc.subject.englycol nucleic acids
dc.subject.enNucleosides
dc.subject.enxeno-nucleic acids
dc.titleFerrocenyl GNA Nucleosides: A Bridge between Organic and Organometallic Xeno-nucleic Acids
dc.typeJournalArticle
dspace.entity.typePublication