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

Ota Masashi, Saito-Tarashima Noriko, Minakawa Noriaki

doi:10.5059/yukigoseikyokaishi.78.446

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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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<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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Journal of Synthetic Organic Chemistry, Japan

Journal of Synthetic Organic Chemistry, Japan 78 (5), 446-455, 2020-05-01

The Society of Synthetic Organic Chemistry, Japan

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