Chemistry of Triazole-Linked Analogue of Nucleic Acids

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  • トリアゾール連結人工核酸の化学
  • トリアゾール レンケツ ジンコウ カクサン ノ カガク

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Replacement of internucleoside phosphodiester linkages of DNA or RNA with non-natural structures would generate intriguing oligonucleotides with functions that could explore the field of medicinal chemistry, chemical biology and materials science. The Nature’s choice of phosphate for the internucleoside linkage is so divine that allows the connection and cleavage of the oligonucleotides at will. When chemists wish to explore the tailor-made variants, an elaborate design of molecular structures is required: an easy synthetic access to the monomeric units, efficient elongation processes, and duplex- or multiplex-forming strands. In this account, we overview the progress of our efforts over the past half a decade on the development of non-natural oligonucleotides with an internucleosidic modification. Adopting an effective reaction from the click chemistry, copper-catalyzed Huisgen cycloaddition, we designed and synthesized the new analogues, triazole-linked DNA and RNA(TLDNA/TLRNA). The robust synthesis supported the concise synthesis of oligonucleotides with triazole-linkages and the development of their functions in bioorganic and materials chemistry.

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