Kogami Masakazu, Koketsu Mamoru
Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.
Org Biomol Chem. 2015 Sep 28;13(36):9405-17. doi: 10.1039/c5ob01316j. Epub 2015 Aug 6.
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.
在本文中，我们报道了一种基于2-(三甲基硅基)乙基（TSE）硒基作为硒化供体来合成5'-硒修饰核苷的通用方法。我们通过将各种官能团直接引入5'-TSE-硒代核苷中，证明了该方法的广泛实用性。这种原创方法为这些化合物的制备提供了额外的优势，如高官能团耐受性、各种亲电试剂易于获得、条件温和、操作简单且产率良好。通过合成作为甲基转移酶化学报告物的硒代腺苷-L-硒代甲硫氨酸（SeAM），进一步证明了该方法的实用性。
