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

Nishizono, Naozumi; Sumita, Yuji; Ueno, Yoshihito et al.

Nucleic Acids Research, 1998, 26(22), 5067-5072

Permalink : https://hdl.handle.net/2115/46964

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アクセス権
open access
URI
https://hdl.handle.net/2115/46964
タイトル
Effects of 2'-O-(trifluoromethyl)adenosine on oligodeoxynucleotide hybridization and nuclease stability
著者
Nishizono, Naozumi ; Sumita, Yuji ; Ueno, Yoshihito ; Matsuda, Akira
著者名
Nishizono, Naozumi
著者名
Sumita, Yuji
著者名
Ueno, Yoshihito
著者名
Matsuda, Akira
言語
英語
発行日
1998-11
出版者
Oxford University Press
収録物名
Nucleic Acids Research
巻(号)
26(22)
ページ
5067-5072
抄録
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.
資源タイプ
学術雑誌論文
出版タイプ
Version of Record
EISSN
1362-4962
関連情報 (isIdenticalTo)
出版社版DOI
https://doi.org/10.1093/nar/26.22.5067