Naslov
NMR evidence of regioselective ferrocenoylation of nucleobases

Autori
Vrček, Valerije ; Šakić, Davor ; Havaić, Valentina ; Djaković, Senka ; Lapić, Jasmina

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Pharma NMR Conference - Application of NMR Spectroscopy in Pharmaceutical Industry / Novak, Predrag ; Tomišić, Vladislav ; Bregović, Nikola - Zagreb : International Association of Physical Chemists (IAPC), 2015, 40-40

Skup
Pharma NMR Conference - Application of NMR Spectroscopy in Pharmaceutical Industry

Mjesto i datum
Rovinj, Hrvatska, 23.09.2015. - 25.09.2015

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
DFT; ferrocene; nucleoside; NMR

Sažetak
Uracil, thymine, and 5-fluorouracil (5-FU) have been ferrocenoylated selectively at N1-position. Regioselectivity of these reactions have been analyzed in details by NMR spectroscopy and quantum chemical calculations. 1H and 19F NMR spectra of reaction mixtures (Figure), and 13C NMR and 2D NOESY spectra of products, confirm the formation of the N1-isomer only. The reaction between uracil/thymine and FcCOCl (Fc = ferrocene) results in the ferrocenoylated product in which C5 signal is shifted ca. 3 ppm downfield compared to the corresponding signal of the parent nucleobases, which is indicative of N1-substitution. This experimental observation is supported by GIAO-NMR calculations for N1- and N3-substituted structures and for the parent pyrimidine bases. Relative difference between calculated 57Fe NMR chemical shifts in N1- and N3-ferrocenoylated nucleobases is less than 18 ppm. This suggests that 57Fe NMR is not a sensitive tool to probe the preferred site of ferrocenoylation in pyrimidine bases. Preliminary results show that prepared ferrocene-nucleoside conjugates exhibit promising bioactivities.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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