Synthesis and properties of oligonucleotides bearing thymidine derivatives with 1,6-dioxaspiro[4.5]decane skeleton
Synthesis and properties of oligonucleotides bearing thymidine derivatives with 1,6-dioxaspiro[4.5]decane skeleton
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1,6-二氧杂螺[4.5]癸烷骨架胸苷衍生物寡核苷酸的合成及性质
DOI：
10.1016/j.bmc.2020.115966
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发表时间：
2021
影响因子：
3.5
通讯作者：
Hari Yoshiyuki
中科院分区：
文献类型：
--
作者：
Osawa Takashi;Kawaguchi Miho;Jang Ye-Jin;Ito Yuta;Hari Yoshiyuki
合成了在C4 α-位上带有螺缩醛部分的胸苷衍生物（5 β R-螺-胸苷和5 β S-螺-胸苷）并掺入寡核苷酸中。两种寡核苷酸的双链体和三链体形成能力从UV熔解实验进行了评价。具有5个S-螺环修饰的寡核苷酸可以与互补RNA和DNA形成热稳定的双链体;然而，5个R-螺环修饰显著降低了双链体和三链体的热稳定性。具有这些螺-胸苷的寡核苷酸显示出对酶促降解的显著高抗性。
Thymidine derivatives bearing spiroacetal moieties on the C4ʹ-position (5ʹR-spiro-thymidine and 5ʹS-spiro-thymidine) were synthesized and incorporated into oligonucleotides. The duplex- and triplex-forming abilities of both the oligonucleotides were evaluated from UV melting experiments. Oligonucleotides with the 5ʹS-spiro modifications could form thermally stable duplexes with complementary RNA and DNA; however, the 5ʹR-spiro modification significantly decreased the thermal stabilities of the duplexes and triplexes. Oligonucleotides with these spiro-thymidines showed significantly high resistance towards enzymatic degradation.