[Polynucleotides and their components in the process of aromatic nucleophilic substitution. I. Chemistry and dynamics of nucleotide arylation with pentafluoropyridine. Intermediate product ofr molecular design of nucleic acid analogs].
Pentafluoropyridine reacts with thymidine, adenosine, and uridine hydroxy groups to give quantitative yields of the corresponding nucleoside di- and triaryl ethers. The nucleophilic substitution reactions proceed successively and in parallel, with the slowest step being the nucleophilic substitution of the nucleoside secondary hydroxyls. The resulting ethers contain tetrafluoropyridyl moieties, which could be smoothly modified by nucleophilic substitution of fluorine atoms. The ethers are useful intermediate synthons (both isolated and in situ) for molecular design of oligonucleotide analogues. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2004, vol. 30, no. 1; see also http://www.maik.ru.
Litvak
V V
VV
Institute of Bioorganic Chemistry, Siberian Division, Russian Academy of Sciences, pr. akademika Lavrent'eva 8, Novosibirsk, 630090 Russia. litvak@niboch.nsc.ru
Maĭnagashev
I Ia
IIa
Bukhanets
O G
OG
D015195:Drug Design; D008239:Lysine / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D009696:Nucleic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D009705:Nucleosides / Q000737:chemistry*; D011119:Polynucleotides / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D005466:Fluorocarbons
D008239:Lysine; D009696:Nucleic Acids; D009705:Nucleosides; D011119:Polynucleotides; D011725:Pyridines; C486857:pentafluoropyridine; D005466:Fluorocarbons