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Synthesis, thermal stability and resistance to enzymatic hydrolysis of the oligonucleotides containing 5-(N-aminohexyl)carbamoyl-2'-O-methyluridines.含5-(N-氨基己基)氨基甲酰基-2'-O-甲基尿苷的寡核苷酸的合成、热稳定性及对酶促水解的抗性
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2'-O-（三氟甲基）腺苷对寡脱氧核苷酸杂交和核酸酶稳定性的影响。

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

作者信息

Nishizono N, Sumita Y, Ueno Y, Matsuda A

机构信息

Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.

出版信息

Nucleic Acids Res. 1998 Nov 15;26(22):5067-72. doi: 10.1093/nar/26.22.5067.

DOI:10.1093/nar/26.22.5067
PMID:9801301
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC147957/
Abstract

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.

摘要

描述了含2'-O-(三氟甲基)腺苷(2)的寡脱氧核苷酸(ODN)的合成及性质。通过分别用聚(氟化氢)吡啶鎓在1,3-二溴-5,5-二甲基乙内酰脲存在下处理2'-O-[(甲硫基)硫代羰基]-3',5'-O-(1,1,3,3-四异丙基二硅氧烷-1,3-二基)(TIPDS)腺苷(4)或N6,N6-(二苯甲酰基)-2'-O-[(甲硫基)硫代羰基]-3',5'-O-(TIPDS)-腺苷(5)，以22%或32%的产率获得2'-O-(三氟甲基)腺苷(2)或N6-(苯甲酰基)-2'-O-(三氟甲基)腺苷(6)。核苷2被掺入到DNA十六聚体中。含2的ODN降低了与其互补DNA双链体的热稳定性，但提高了与其互补RNA双链体的热稳定性。此外，含2的ODN比未修饰的ODN对蛇毒磷酸二酯酶的抗性略强。