Rapid Alkene-Alkene Photo-Cross-Linking on the Base-Flipping-Out Field in Duplex DNA

被引：8

作者：

Abdelhady, Ahmed Mostafa ^{[1
,2
,3
]}

Onizuka, Kazumitsu ^{[1
,4
]}

Ishida, Kei ^{[1
,2
]}

Yajima, Sayaka ^{[1
,2
]}

Mano, Eriko ^{[1
]}

Nagatsugi, Fumi ^{[1
,2
]}

机构：

[1] Tohoku Univ, Inst Multidisciplinary Res Adv Mat, Sendai, Miyagi 9808577, Japan

[2] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

[3] Al Azhar Univ, Fac Sci, Dept Chem, Cairo 11884, Egypt

[4] Tohoku Univ, Div Estab Frontier Sci Org Adv Studies, Sendai, Miyagi 9808577, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 05期

基金：

日本学术振兴会;

关键词：

IN-SITU HYBRIDIZATION; LINKED DNA; RNA; EFFICIENT; FLUORESCENCE; PROBES; PAIR; OLIGODEOXYRIBONUCLEOTIDES; OLIGONUCLEOTIDES; STABILITY;

D O I：

10.1021/acs.joc.1c01498

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Specific chemical reactions by enzymes acting on a nucleobase are realized by flipping the target base out of the helix. Similarly, artificial oligodeoxynucleotides (ODNs) can also induce the base flipping and a specific chemical reaction. We now report an easily prepared and unique structure-providing photo-cross-linking reaction by taking advantage of the base-flipping-out field formed by alkene-type base-flipping-inducing artificial bases. Two 3-arylethenyl-S-methyl-2-pyridone nucleosides with the Ph or An group were synthesized and incorporated into the ODNs. We found that the two Ph derivatives provided the cross-linked product in a high yield only by a 10 s photoirradiation when their alkenes overlap each other in the duplex DNA. The highly efficient reaction enabled forming a cross-linked product even when using the duplex with a low T-m value.

引用

页码：2267 / 2276

页数：10

共 48 条

[1] Synthesis of crosslinked 2′-OMe RNA duplexes and their application for effective inhibition of miRNA function [J].