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Pregled bibliografske jedinice broj: 921375

Ferrocenyl GNA nucleosides: a bridge between organic and organometallic xeno-nucleic acids


Kowalski, Konrad; Skiba Joanna; Yuan, Qing; Hildebrandt, Alexander; Trzybinski, Damian; Wozniak, Krzystof; Balogh, Ria; Gyurcsik, Bela; Vrček, Valerije
Ferrocenyl GNA nucleosides: a bridge between organic and organometallic xeno-nucleic acids // ChemPlusChem, 83 (2018), 2; 77-86 doi:10.1002/cplu.201700551 (međunarodna recenzija, članak, znanstveni)


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Naslov
Ferrocenyl GNA nucleosides: a bridge between organic and organometallic xeno-nucleic acids

Autori
Kowalski, Konrad ; Skiba Joanna ; Yuan, Qing ; Hildebrandt, Alexander ; Trzybinski, Damian ; Wozniak, Krzystof ; Balogh, Ria ; Gyurcsik, Bela ; Vrček, Valerije

Izvornik
ChemPlusChem (2192-6506) 83 (2018), 2; 77-86

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
ferrocene ; xeno nucleic acid ; glycol nucleic acid ; nucleosides ; bioorganometallics

Sažetak
A Sharpless asymmetric dihydroxylation reaction was applied to obtain ferrocenyl-GNA nucleosides. These are the first known representatives of redox active organometallic GNA ever reported and contribute to the expanding of GNA family tree. The (S, R) and (R, S) absolute configuration of the chiral carbon atoms in the Fc-GNA nucleosides was assigned by the X-ray crystallography of the methylated derivatives. Furthermore, CD spectroscopy of the methylated derivatives was conducted. The CD spectra are mirror-like images, reflecting the enantiomeric relationship between the compounds. Electrochemical studies reveal that each of the Fc-GNA nucleosides undergoes a reversible one-electron oxidation at a potential of -25 mV (for non-methylated derivatives) and 75 mV (for methylated derivatives), respectively. Further studies are needed to probe the usefulness of the herein reported Fc-GNA nucleosides as building blocks for oligonucleotide synthesis.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
HRZZ-IP-2016-06-1137 - Kvantno-kemijski dizajn, priprava i biološka svojstva organometalnih derivata nukleobaza (Valerije Vrček, HRZZ)

Ustanove
Farmaceutsko-biokemijski fakultet, Zagreb

Profili:

Avatar Url Valerije Vrček (autor)

Citiraj ovu publikaciju

Kowalski, Konrad; Skiba Joanna; Yuan, Qing; Hildebrandt, Alexander; Trzybinski, Damian; Wozniak, Krzystof; Balogh, Ria; Gyurcsik, Bela; Vrček, Valerije
Ferrocenyl GNA nucleosides: a bridge between organic and organometallic xeno-nucleic acids // ChemPlusChem, 83 (2018), 2; 77-86 doi:10.1002/cplu.201700551 (međunarodna recenzija, članak, znanstveni)
Kowalski, K., Skiba Joanna, Yuan, Q., Hildebrandt, A., Trzybinski, D., Wozniak, K., Balogh, R., Gyurcsik, B. & Vrček, V. (2018) Ferrocenyl GNA nucleosides: a bridge between organic and organometallic xeno-nucleic acids. ChemPlusChem, 83 (2), 77-86 doi:10.1002/cplu.201700551.
@article{article, year = {2018}, pages = {77-86}, DOI = {10.1002/cplu.201700551}, keywords = {ferrocene, xeno nucleic acid, glycol nucleic acid, nucleosides, bioorganometallics}, journal = {ChemPlusChem}, doi = {10.1002/cplu.201700551}, volume = {83}, number = {2}, issn = {2192-6506}, title = {Ferrocenyl GNA nucleosides: a bridge between organic and organometallic xeno-nucleic acids}, keyword = {ferrocene, xeno nucleic acid, glycol nucleic acid, nucleosides, bioorganometallics} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • Arts & Humanities Citation Index (A&HCI)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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