Synthesis of the Oligoribonucleotides Incorporating 8-Oxo-Guanosine and Evaluation of their Base Pairing Properties
Synthesis of the Oligoribonucleotides Incorporating 8-Oxo-Guanosine and Evaluation of their Base Pairing Properties
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DOI：
10.1080/15257770.2013.767461
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发表时间：
2013-01-01
影响因子：
1.3
通讯作者：
Sasaki, Shigeki
中科院分区：
文献类型：
--
作者：
Koga, Yohei;Taniguchi, Yosuke;Sasaki, Shigeki
合成了N-二异丙基亚磷酰胺(5)，作为合成核糖核酸的新亚磷酰胺前驱体单元。化合物5被成功地掺入到RNA序列的中间，合成的RNA通过MALDI-TOF质量测量进行了鉴定。对它们的性质进行了评价，以形成RNA双链和RNA/DNA异源双链。含有8-oxo-G的基因1和4可以与Rc或DC以反构象形式形成碱基对，也可以与Ra或da以同步构象以RNA双链或RNA/DNA异源双链的形式相互作用。因此，所描述的合成方法对于合成含有8-oxo-G的ORN是一种有用的步骤，并有助于研究RNA中的8-oxo-G。
6-O-7-N-Bis(diphenylcarbamoyl)-2-N-phenoxyacetyl-5'-O-dimethoxytrityl-2'-O-{[(triisopropyl-silyl)oxy]methyl}-8-oxoguanosine-3'-yl-beta-cyanoethyl-N,N-diisopropylphosphoramidite (5) was synthesized as a new phosphoramidite precursor unit for the synthesis of RNA. Compound 5 was successfully incorporated into the middle of the RNA sequences, and the synthesized RNAs were identified by MALDI-TOF mass measurements. Their properties were evaluated for formation of the RNA duplex and RNA/DNA heteroduplex. ORNs 1 and 4 containing 8-oxo-G can form base pairs with rC or dC in an anti conformation, while it can also interact with rA or dA in a syn conformation in the RNA duplex or RNA/DNA heteroduplex. The described synthetic method is therefore a useful procedure for the synthesis of ORN containing 8-oxo-G and contributes to the study of 8-oxo-G in RNA.