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

Naozumi Nishizono | Zendy; Y. Sumita | Zendy; Yoshihito Ueno | Zendy; Akira Matsuda | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

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

Author(s) -

Naozumi Nishizono,

Y. Sumita,

Yoshihito Ueno,

Akira Matsuda

Publication year - 1998

Publication title -

nucleic acids research

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 9.008

H-Index - 537

eISSN - 1362-4954

pISSN - 0305-1048

DOI - 10.1093/nar/26.22.5067

Subject(s) - adenosine , trifluoromethyl , biology , nucleoside , nuclease , thermal stability , dna , nucleic acid , stereochemistry , biochemistry , chemistry , organic chemistry , alkyl

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.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research