Synthesis of selenium-derivatized nucleosides and oligonucleotides for X-ray crystallography.
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.
Carrasco
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Department of Chemistry, Brooklyn College, The Graduate School of The City University of New York, 11210, USA.
Ginsburg
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D
Du
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Huang
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Z
D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D018036:Selenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D009705:Nucleosides; D009841:Oligonucleotides; D018036:Selenium Compounds