Carrasco N, Ginsburg D, Du Q, Huang Z
Department of Chemistry, Brooklyn College, The Graduate School of The City University of New York, 11210, USA.
Nucleosides Nucleotides Nucleic Acids. 2001 Sep;20(9):1723-34. doi: 10.1081/NCN-100105907.
We report here the synthesis of nucleoside and oligonucleotide analogs containing selenium, which serves as an anomalous scattering center to enable MAD phase determination in nucleotide X-ray crystallography. We have developed a phase transfer approach to introduce the selenium functionality in A, C, G, T, and U nucleosides at 5'-positions. In the incorporation of the selenium functionality, the leaving groups (bromide, mesyl, and tosyl) were readily displaced by sodium selenide, sodium diselenide, and sodium methyl selenide with yields higher than 90%. Selenium-derivatized oligonucleotides have been synthesized via phosphoramidite chemistry.
我们在此报告含硒核苷和寡核苷酸类似物的合成，硒作为反常散射中心，可用于核苷酸X射线晶体学中的多波长反常散射（MAD）相位测定。我们开发了一种相转移方法，在A、C、G、T和U核苷的5'-位引入硒官能团。在引入硒官能团的过程中，离去基团（溴化物、甲磺酰基和对甲苯磺酰基）很容易被硒化钠、二硒化钠和甲基硒化钠取代，产率高于90%。已通过亚磷酰胺化学合成了硒衍生化的寡核苷酸。
