Photoreactivities of 5-Bromouracil-containing RNAs

Photoreactivities of 5-Bromouracil-containing RNAs
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含 5-溴尿嘧啶 RNA 的光反应性

DOI:
10.1016/j.bmc.2012.11.010
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发表时间:
2013
期刊:
Bioorg Med Chem
影响因子:
--
通讯作者:
Sugiyama H.
Sugiyama H.
中科院分区:
--
文献类型:
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作者:
Morinaga H;Kizaki S;Takenaka T;Kanesato S;Sannohe Y;Tashiro R;Sugiyama H.

文献摘要

相似文献

5-将溴尿嘧啶(BrU)掺入到三种合成RNA中,用HPLC和MS分析了含BrU的RNA的光辐射产物。A型RNA中的r(GCABrUGC)2和r(CGAABrUUGC)/r(GCAAUUCG)在5′端产生相应的2′-酮腺苷(ketoA)产物,如r(GCketoAUGC)和r(CGAketoAUUGC)。Z型RNA中r(CGCGBrUGCG)/r(CmGCACmGCG)的光照射产生2′-酮基鸟苷(ketoG)产物r(CGCketoGUGCG),而A型RNA中r(CGCGBrUGCG)/r(CmGCACmGCG)的光照射几乎没有产物。目前的结果清楚地表明,光化学产生的尿嘧啶-5-基自由基的氢(H)提取选择性地发生在C2′位,以提供2′-酮RNA产物。
5-Bromouracil (BrU) was incorporated into three types of synthetic RNA and the products of the photoirradiatedBrU-containing RNAs were investigated using HPLC and MS analysis. The photoirradiation of r(GCABrUGC)2and r(CGAABrUUGC)/r(GCAAUUCG) in A-form RNA produced the corresponding 2′-keto adenosine (ketoA) product at the 5′-neighboring nucleotide, such as r(GCketoAUGC) and r(CGAketoAUUGC), respectively. The photoirradiation of r(CGCGBrUGCG)/r(CmGCACmGCG) in Z-form RNA produced the 2′-keto guanosine (ketoG) product r(CGCketoGUGCG), whereas almost no products were observed from the photoirradiation of r(CGCGBrUGCG)/r(CmGCACmGCG) in A-form RNA. The present results indicate clearly that hydrogen (H) abstraction by the photochemically generated uracil-5-yl radical selectively occurs at the C2′ position to provide a 2′-keto RNA product.