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Effects of 2'-O-(trifluoromethyl)adenosine on oligodeoxynucleotide hybridization and nuclease stability
| Title: | Effects of 2'-O-(trifluoromethyl)adenosine on oligodeoxynucleotide hybridization and nuclease stability |
| Authors: | Nishizono, Naozumi Browse this author | | Sumita, Yuji Browse this author | | Ueno, Yoshihito Browse this author | | Matsuda, Akira Browse this author |
| Issue Date: | Nov-1998 |
| Publisher: | Oxford University Press |
| Journal Title: | Nucleic Acids Research |
| Volume: | 26 |
| Issue: | 22 |
| Start Page: | 5067 |
| End Page: | 5072 |
| Publisher DOI: | 10.1093/nar/26.22.5067 |
| Abstract: | 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. |
| Type: | article |
| URI: | http://hdl.handle.net/2115/46964 |
| Appears in Collections: | 薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 松田 彰
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