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

The synthesis and properties of oligodeoxynucleotides (ODNs) containing 2′-O-(trifluoromethyl)adenosine (2) are described. 2′-O-(Trifluoromethyl)adenosine (2) or N6-(benzoyl)-2′-O-(trifluoromethyl)adenosine (6) was obtained in 22 or 32% yield by treating 2′-O-[(methylthio) thiocarbonyl]-3′,5′-O-(1,1...

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Bibliographic Details
Published in:Nucleic acids research 1998-11, Vol.26 (22), p.5067-5072
Main Authors: Nishizono, Naozumi, Sumita, Yuji, Ueno, Yoshihito, Matsuda, Akira
Format: Article
Language:English
Subjects:
Adenosine - analogs & derivatives
Adenosine - pharmacology
Animals
Base Sequence
Circular Dichroism
Drug Stability
In Vitro Techniques
Nucleic Acid Hybridization
Oligodeoxyribonucleotides - chemical synthesis
Oligodeoxyribonucleotides - chemistry
Phosphodiesterase I
Phosphoric Diester Hydrolases
Thermodynamics
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Summary:The synthesis and properties of oligodeoxynucleotides (ODNs) containing 2′-O-(trifluoromethyl)adenosine (2) are described. 2′-O-(Trifluoromethyl)adenosine (2) or N6-(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 N6,N6-(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.
ISSN:0305-1048
1362-4962
DOI:10.1093/nar/26.22.5067