Osawa Takashi, Hari Yoshiyuki, Dohi Masakazu, Matsuda Yuya, Obika Satoshi
Graduate School of Pharmaceutical Sciences, Osaka University , 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
Core Research for Evolutional Science and Technology (CREST), Japan Sciences and Technology Agency (JST) , 7 Gobancho, Chiyoda-ku, Tokyo 102-0076, Japan.
J Org Chem. 2015 Nov 6;80(21):10474-81. doi: 10.1021/acs.joc.5b01425. Epub 2015 Oct 14.
A novel 2'-O,4'-C-bridged nucleic acid, 3,4-dihydro-2H-pyran bridge moiety (DpNA), with a dioxabicyclo[3.2.1]oct-3-ene ring was designed. Construction of the dihydropyran bridge was achieved by dehydration of a six-membered hemiacetal ring, and the DpNA monomer was synthesized in 10 steps from 5-methyluridine (total yield 9%). The synthesized DpNA monomer was incorporated into oligonucleotides to examine the properties of the modified oligonucleotides. The DpNA-modified oligonucleotides possessed high affinity toward ssRNA and were more resistant to nucleases compared to the corresponding natural oligonucleotide.
设计了一种新型的2'-O,4'-C-桥连核酸，即具有二氧杂双环[3.2.1]辛-3-烯环的3,4-二氢-2H-吡喃桥部分（DpNA）。二氢吡喃桥的构建是通过六元半缩醛环的脱水实现的，DpNA单体由5-甲基尿苷经10步合成（总产率9%）。将合成的DpNA单体掺入寡核苷酸中以研究修饰寡核苷酸的性质。与相应的天然寡核苷酸相比，DpNA修饰的寡核苷酸对单链RNA具有高亲和力且对核酸酶更具抗性。
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