An efficient method for the synthesis of selenium modified nucleosides: Its application to the synthesis of Se-adenosyl-L-selenomethionine (SeAM)
An efficient method for the synthesis of selenium modified nucleosides: Its application to the synthesis of Se-adenosyl-L-selenomethionine (SeAM)
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一种高效合成硒修饰核苷的方法：其在硒-腺苷-L-硒代蛋氨酸（SeAM）合成中的应用
DOI：
10.1039/c5ob01316j
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发表时间：
2015
影响因子：
3.2
通讯作者：
Masakazu Kogami and Mamoru Koketsu
中科院分区：
文献类型：
--
作者：
Yuki Takeda;Koichi Narita;Tadashi Katoh;清水洋平;Masakazu Kogami and Mamoru Koketsu
以2-（三甲基硅基）乙基（TSE）硒基为硒化供体，探索了一种合成5′-硒修饰核苷的通用方法。我们通过直接将各种官能团引入到5′-TSE-硒代糖苷中，证明了这种方法的广泛实用性。这种新颖的方法为制备这些化合物提供了额外的优点，例如高官能团耐受性，各种亲电试剂的易得性，条件温和，操作简单，产率高。这种方法的效用进一步证明了硒-腺苷-L-硒代蛋氨酸（SeAM）作为甲基转移酶的化学报告的合成。
In this paper, we report that a versatile method for the synthesis of 5′-selenium modified nucleosides has been explored on the basis of a 2-(trimethylsilyl)ethyl (TSE) selenyl group as a selenating donor. We demonstrate the broad utility of this method through direct introduction of various functional groups into 5′-TSE-selenonucleosides. This original method offers additional advantages for the preparation of these compounds, such as high functional group tolerance, ready availability of various electrophilic reagents, mild conditions, simple operation, and good yields. The utility of this approach is further demonstrated by the synthesis of Se-adenosyl-L-selenomethionine (SeAM) as a chemical reporter for methyltransferases.