Chemistry for Nucleic Acid Analogs Having Sulfur and Selenium Atoms in Place of Furanose Ring Oxygen

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  • フラノース環酸素原子を硫黄，セレン原子に置換した核酸誘導体の有機合成化学
  • フラノースカン サンソ ゲンシ オ イオウ,セレン ゲンシ ニ チカン シタ カクサン ユウドウタイ ノ ユウキ ゴウセイ カガク

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Abstract

<p>To date, a number of chemically modified oligonucleotides (ONs) have been designed for use in nucleic acids-based therapeutics. In our group, we have been intensely working on the synthesis of 4’-thio and 4’-seleno ONs having sulfur or selenium atoms in place of furanose ring oxygen. To prepare 4’-thio and 4’-seleno ribonucleosides, we applied the Pummerer reaction of 4-thio or 4-seleno sugar with nucleobases, and the resulting 4’-thio and 4’-seleno ribonucleoside units were incorporated into ONs. Under the standard phosphoramidite conditions, 4’-thioRNA was obtained in good yields. While 4’-selnoRNA was given in very low yields. We carefully investigated ON synthesis containing 4’-selenoribonucleosides under standard phosphoramidite conditions. As a result, we found the unexpected strand-break occurred during oxidation step using I2. On the basis of this finding, we succeeded in the first synthesis of a fully modified 4’-selenoRNA by using tert-butyl hydroperoxide as an alternative oxidant.</p>

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