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Pregled bibliografske jedinice broj: 875389

1, 1'-Bis(thymine)ferrocene Nucleoside : Synthesis and Study of Its Stereoselective Formation


Kowalski, Konrad; Anisimov, Iurii; Salomon, Sebastian; Hildebrandt, Alexander; Lang, Heinrich; Trzybinski, Damian; Wozniak, Krzysztof; Šakić, Davor; Vrček, Valerije
1, 1'-Bis(thymine)ferrocene Nucleoside : Synthesis and Study of Its Stereoselective Formation // ChemPlusChem, 82 (2017), 6; 859-866 doi:10.1002/cplu.201700215 (međunarodna recenzija, članak, znanstveni)


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Naslov
1, 1'-Bis(thymine)ferrocene Nucleoside : Synthesis and Study of Its Stereoselective Formation

Autori
Kowalski, Konrad ; Anisimov, Iurii ; Salomon, Sebastian ; Hildebrandt, Alexander ; Lang, Heinrich ; Trzybinski, Damian ; Wozniak, Krzysztof ; Šakić, Davor ; Vrček, Valerije

Izvornik
ChemPlusChem (2192-6506) 82 (2017), 6; 859-866

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

Ključne riječi
organometallic chemistry, electrochemistry, bioactive compounds, reaction mechanism, DFT

Sažetak
The synthesis of 1, 1'-bis(thymine)ferrocene nucleoside is reported. This molecule was obtained in a two-step synthetic methodology including a Michael addition reaction of 1, 1'-bis(3-chloropropionyl)ferrocene with thymine as a first step. In the 2nd step, the two prochiral carbonyl functionalities in the Michael adduct were reduced to hydroxyl functionalities. Reduction proceeds in a highly stereoselective fashion, yielding the ferrocenyl nucleoside as a racemic mixture consisting of the (R, R) and the (S, S) isomers. The absolute configuration at the chiral carbon atoms was unambiguously confirmed by single-crystal X-ray diffraction analysis for the methyl derivative of the nucleoside. The mechanism of reduction was investigated with DFT calculations. The two critical minima, prereactive complex and semi-reduced intermediate, and two corresponding transition states were located in support of the observed diastereoselectivity. The redox properties of 1, 1'-bis(thymine)ferrocene nucleoside, its precursor and congeners were investigated using cyclic voltammetry.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
6499 - Kvantno-kemijski dizajn, priprava i biološka svojstva organometalnih derivata nukleobaza (Valerije Vrček, HRZZ)

Ustanove
Farmaceutsko-biokemijski fakultet, Zagreb

Profili:

Avatar Url Valerije Vrček (autor)

Avatar Url Davor Šakić (autor)

Citiraj ovu publikaciju

Kowalski, Konrad; Anisimov, Iurii; Salomon, Sebastian; Hildebrandt, Alexander; Lang, Heinrich; Trzybinski, Damian; Wozniak, Krzysztof; Šakić, Davor; Vrček, Valerije
1, 1'-Bis(thymine)ferrocene Nucleoside : Synthesis and Study of Its Stereoselective Formation // ChemPlusChem, 82 (2017), 6; 859-866 doi:10.1002/cplu.201700215 (međunarodna recenzija, članak, znanstveni)
Kowalski, K., Anisimov, I., Salomon, S., Hildebrandt, A., Lang, H., Trzybinski, D., Wozniak, K., Šakić, D. & Vrček, V. (2017) 1, 1'-Bis(thymine)ferrocene Nucleoside : Synthesis and Study of Its Stereoselective Formation. ChemPlusChem, 82 (6), 859-866 doi:10.1002/cplu.201700215.
@article{article, year = {2017}, pages = {859-866}, DOI = {10.1002/cplu.201700215}, keywords = {organometallic chemistry, electrochemistry, bioactive compounds, reaction mechanism, DFT}, journal = {ChemPlusChem}, doi = {10.1002/cplu.201700215}, volume = {82}, number = {6}, issn = {2192-6506}, title = {1, 1'-Bis(thymine)ferrocene Nucleoside : Synthesis and Study of Its Stereoselective Formation}, keyword = {organometallic chemistry, electrochemistry, bioactive compounds, reaction mechanism, DFT} }

Časopis indeksira:


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


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