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N2,N2,7-三甲基鸟苷帽衍生物的合成。

Synthesis of N2, N2, 7-trimethylguanosine cap derivatives.

作者信息

Iwase R, Sekine M, Tokumoto Y, Ohshima Y, Hata T

机构信息

Department of Life Chemistry, Tokyo Institute of Technology, Yokohama, Japan.

出版信息

Nucleic Acids Res. 1989 Nov 25;17(22):8979-89. doi: 10.1093/nar/17.22.8979.

DOI:10.1093/nar/17.22.8979
PMID:2587250
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC335107/
Abstract

Several derivatives of N2,N2-7-trimethylguanosine (m3(2,2,7G)-cap, which was found at the 5' ends of small nuclear RNAs, were synthesized by use of S-phenyl N2,N2,7-trimethylguanosine 5'-phosphorothioate (PhSpm3(2,2,7)G) as a key intermediate. This compound was activated by iodine in the presence of phosphoric acid and diphosphoric acid to give N2,N2,7-trimethylguanosine-5'-diphosphate (ppm3(2,2,7)G) and 5'-triphosphate (ppm3(2,2,7)G), respectively. Similar reactions of PhSpm3(2,2,7)G with ADP and GDP gave capped dinucleoside triphosphates, m3(2,2,7)G5'pppA and m3(2,2,7)G5'pppG, respectively.

摘要

通过使用S-苯基N2,N2,7-三甲基鸟苷5'-硫代磷酸酯(PhSpm3(2,2,7)G)作为关键中间体,合成了几种在小核RNA 5'端发现的N2,N2-7-三甲基鸟苷(m3(2,2,7G)-帽)衍生物。该化合物在磷酸和焦磷酸存在下用碘活化,分别得到N2,N2,7-三甲基鸟苷-5'-二磷酸(ppm3(2,2,7)G)和5'-三磷酸(ppm3(2,2,7)G)。PhSpm3(2,2,7)G与ADP和GDP的类似反应分别得到带帽的二核苷三磷酸,即m3(2,2,7)G5'pppA和m3(2,2,7)G5'pppG。

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本文引用的文献

1
Chemical synthesis of the 5'-terminal part bearing cap structure of messenger RNA of cytoplasmic polyhedrosis virus (CPV): m7G5'pppAmpG and m7G5'pppAmpGpU.细胞质多角体病毒(CPV)信使核糖核酸(mRNA)5′末端带有帽结构部分的化学合成:m7G5′pppAmpG和m7G5′pppAmpGpU
Nucleic Acids Res. 1984 Mar 26;12(6):2939-54. doi: 10.1093/nar/12.6.2939.
2
Purine nucleosides. 8. The synthesis of 2-fluoro- and 2-chloroinosine and certain derived purine nucleosides.
J Org Chem. 1966 Oct;31(10):3258-62. doi: 10.1021/jo01348a037.
3
Trans-spliced leader RNA exists as small nuclear ribonucleoprotein particles in Caenorhabditis elegans.在秀丽隐杆线虫中,反式剪接前导RNA以小核核糖核蛋白颗粒的形式存在。
Nature. 1988 Oct 6;335(6190):556-9. doi: 10.1038/335556a0.
4
The C. elegans trans-spliced leader RNA is bound to Sm and has a trimethylguanosine cap.秀丽隐杆线虫的反式剪接前导RNA与Sm结合,并具有三甲基鸟苷帽。
Cell. 1988 Aug 12;54(4):533-9. doi: 10.1016/0092-8674(88)90075-x.
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Beta-globin mRNAs capped with m7G, m2.7(2)G or m2.2.7(3)G differ in intrinsic translation efficiency.带有m7G、m2.7(2)G或m2.2.7(3)G帽结构的β-珠蛋白mRNA在内在翻译效率上存在差异。
Nucleic Acids Res. 1988 Sep 26;16(18):8953-62. doi: 10.1093/nar/16.18.8953.