機能性人工核酸の創製を目指した新規核酸合成法の開発  [in Japanese] Development of New Methods for Synthesis of Artificial Nucleic Acids having Various Functional Groups  [in Japanese]

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Abstract

Development of effective methods for the synthesis of modified oligonucleotides having various functional groups is highly desirable today. Recently, we developed <i>O</i>-selective phosphorylation named the proton-block method and the activated phosphite method to synthesize modified DNA oligonucleotide having alkaline-labile functional groups. In RNA synthesis without base protection, it was found that <i>O</i>-selectivity of the phosphorylation with P-N bond cleavage using 6-nitro-HOBt was more than 99%. Additionally, development of new protecting groups, which can be removed under mild conditions, such as AzMB, PSC and amidine-type groups was carried out. Furthermore, we developed the effective pyrophosphorylation using O-N phosphoryl rearrangement of phosphoramidite compound mediated by HOBt derivative. This new pyrophosphorylation could be applied to the synthesis of adenylpyrophosphoryl capped and 5’-terminal m<sub>3</sub><sup>2,2,7</sup>Gppp capped oligonucleotides.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 72(8), 899-909, 2014

    The Society of Synthetic Organic Chemistry, Japan

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