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Nucleic Acids Research, Vol 26, Issue 22 5067-5072, Copyright © 1998 by Oxford University Press

ARTICLES

Effects of 2'-O-(trifluoromethyl)adenosine on oligodeoxynucleotide hybridization and nuclease stability

N Nishizono, Y Sumita, Y Ueno and A Matsuda
Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita- 12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.

The synthesis and properties of oligodeoxynucleotides (ODNs) containing 2'- O -(trifluoromethyl)adenosine (2) are described. 2'- O - (Trifluoromethyl)adenosine (2) or N 6-(benzoyl)-2'- O - (trifluoromethyl)adenosine (6) was obtained in 22 or 32% yield by treating 2'- O -[(methylthio)thiocarbonyl]-3',5'- O -(1,1,3, 3- tetraisopropyldisiloxane-1,3-diyl)(TIPDS)adenosine (4) or N 6, N 6- (dibenzoyl)-2'- O -[(methylthio)thiocarbonyl]-3',5'- O -(TIPDS)- adenosine (5), respectively, with pyridinium poly-(hydrogen fluoride) in the presence of 1,3-dibromo-5,5-dimethylhydantoin. Nucleoside 2 was incorporated into DNA hexadecamers. ODNs that contained 2 reduced the thermal stability of duplexes with their complementary DNAs but increased the thermal stability of duplexes with their complementary RNAs. Furthermore, ODNs containing 2 were slightly more resistant to snake venom phosphodiesterase than an unmodified ODN.
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T. Ito, Y. Ueno, Y. Komatsu, and A. Matsuda
Synthesis, thermal stability and resistance to enzymatic hydrolysis of the oligonucleotides containing 5-(N-aminohexyl)carbamoyl-2'-O-methyluridines
Nucleic Acids Res., May 15, 2003; 31(10): 2514 - 2523.
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