Karwowski Boleslaw, Seio K, Sekine M
Department of Life Science, Tokyo Institute of Technology, Japan and JST (Japan Science and Technology Corporation), Japan.
Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):1111-4. doi: 10.1081/ncn-200061895.
We wish to report 4,5-bis(ethoxycarbonyl)-[1,3]dioxolan-2-yl as a new protecting for the 2'-hydroxyl function. Our cyclic orthoester-type group is compatible with the DMTr strategy for oligonucleotide synthesis. This group was introduced to the 2'-hydroxyl group of appropriately protected nucleoside derivatives in good yields under mild acidic conditions. Post-synthetic conversion of the moiety of this protecting group with an amine resulted in formation of a new amide moiety that is more stable to acid deprotection in aqueous solution, but it can still be easily removed by treatment with acids in organic solvents. In this article, we also describe the stability of not only the original and modified protecting groups but also internucleotidic phosphate linkages of protected RNA intermediates under deprotection conditions.
我们希望报道4,5-双（乙氧羰基）-[1,3]二氧戊环-2-基作为2'-羟基官能团的一种新的保护基。我们的环状原酸酯型基团与用于寡核苷酸合成的DMTr策略兼容。在温和酸性条件下，该基团以良好的产率引入到适当保护的核苷衍生物的2'-羟基上。该保护基团部分与胺进行合成后转化，形成了一种新的酰胺部分，其在水溶液中对酸脱保护更稳定，但仍可通过在有机溶剂中用酸处理而轻松去除。在本文中，我们还描述了在脱保护条件下，不仅原始和修饰的保护基团的稳定性，还有受保护的RNA中间体的核苷酸间磷酸酯键的稳定性。
