Year 2005, Month 1 (Section Full Articles, Page 238)
Synthesis and properties of oligodeoxyribonucleotides
containing 2´-O-(2,3-dihydroxypropyl)- and
2´-O-(2-oxoethyl)arabinouridine residues*
T. S. Zatsepin, Yu. M. Ivanova, D. A. Stetsenko, M. J. Gait, and T. S. Oretskaya*
2´-O-(2,3-Dihydroxypropyl)arabinouridine-containing oligodeoxyribonucleotides were
synthesized starting from a new modified nucleoside, viz., 2´-O-(2,3-dihydroxypropyl)arabinouridine, and the corresponding 3´-phosphoramidite. Oxidation of these oligodeoxyribonucleotides with sodium periodate afforded oligonucleotides containing 2´-O-(2-oxoethyl)arabinouridine residues. Subsequent modification of the aldehyde-containing oligonucleotides involved the reactions with 9-hydrazinoacridine and N-aminooxyacetyl peptide and
reductive amination by 4-(1-pyrenyl)butyrohydrazide and biotin hydrazide. Thermal stabilities
of duplexes of modified oligodeoxyribonucleotides with complementary oligodeoxyribonucleotides are slightly lower than those of natural duplexes. Duplexes with complementary
oligoribonucleotides are substantially destabilized.
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