Oligonucleotide containing S-functionalized 2'-deoxy-6-thioguanosine : Facile tools for base-selective and site specific internal modification of RNA
Oligonucleotide containing S-functionalized 2'-deoxy-6-thioguanosine : Facile tools for base-selective and site specific internal modification of RNA
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含有 S-功能化 2-脱氧-6-硫鸟苷的寡核苷酸：用于 RNA 碱基选择性和位点特异性内部修饰的简便工具
DOI：
10.1002/0471142700.nc0449s48
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发表时间：
2012
期刊：
影响因子：
--
通讯作者：
Yosuke Taniguchi
中科院分区：
文献类型：
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作者：
Shigeki Sasaki;Kazumitsu Onizuka;Yosuke Taniguchi
化学修饰的寡核苷酸在基因组研究中发挥着重要作用。修饰的核苷，例如用荧光染料修饰的核苷，可以通过化学合成获得。位点特异性修饰的长核酸通过化学修饰的短寡核苷酸与酶、光化学或催化DNA的连接获得。功能性转移ODN（FT-ODN）含有用2-亚甲基-1，3-二酮基团官能化的2′-脱氧-6-硫代鸟苷（6-thio-dG），其与靶RNA杂交以在pH 7下触发胞嘧啶碱基的4-氨基或在pH 9.4下或在NiCl 2存在下在pH 7.4下触发鸟嘌呤碱基的2-氨基的选择性官能化。特别是，在NiCl 2存在下，在碱性条件或中性条件下的功能转移反应（FTR）快速且选择性地进行，从而导致目标鸟嘌呤的修饰。含乙炔的二酮基团的转移反应产生乙炔修饰的RNA，其可以与各种叠氮化合物进行Cu（I）催化的“点击化学”，用于RNA的高度特异性的内部修饰。协议核酸化学48：4.49.1 - 4.49.16。© 2012年由John Wiley & Sons，Inc.
Chemically modified oligonucleotides play a significant role for genomic research. Modified nucleosides, such as with a fluorescent dye, can be obtained by chemical synthesis. Site‐specifically modified long nucleic acids are obtained by ligation of chemically modified short oligonucleotides with enzyme, photochemistry, or catalytic DNA. The functionality‐transfer ODN (FT‐ODN), which contains 2′‐deoxy‐6‐thioguanosine (6‐thio‐dG) functionalized with the 2‐methyliden‐1,3‐diketone group, is hybridized with the target RNA to trigger the selective functionalization of the 4‐amino group of the cytosine base at pH 7 or the 2‐amino group of the guanine base at pH 9.4 or at pH 7.4 in the presence of NiCl2. In particular, the functionality‐transfer reaction (FTR) under the alkaline conditions or neutral conditions in the presence of NiCl2proceeds rapidly and selectively to lead to the modification of the target guanine. The transfer reaction of the acetylene‐containing diketone group produces the acetylene‐modified RNA, which can be subjected to the Cu(I)‐catalyzed “click chemistry” with a variety of azide compounds for highly specific, internal modification of RNA.Curr. Protoc. Nucleic Acid Chem. 48:4.49.1‐4.49.16. © 2012 by John Wiley & Sons, Inc.