Conformational characteristics of 3'-deoxy-3'-fluoro- and 2',3'-dideoxy-3'-fluororibonucleosides
N. B. Khripach, N. E. Poopeiko, I. Yu. Skorynin, E. V. Borisov
Institute of Bioorganic Chemistry, Academy of Sciences of the Byelorussian SSR, Minsk
Abstract: The conformations of the furanose ring of 3'-deoxy-3'-fluoro- and 2',3'-dideoxy-3'-fluoro-β-D-ribofuranosides of adenine, guanine, cytosine and uracil were determined from the 1H NMR spectra. The introduction of a highly electronegative fluorine atom at 3'-position was shown to stabilize the furanose S-conformation.
Russian Journal of Bioorganic Chemistry 1991, 17 (11):1521-1525