Chemistry of triazole-linked analogue of nucleic acids

Hiroyuki Isobe, Tomoko Fujino

Research output: Contribution to journalReview articlepeer-review

1 Citation (Scopus)

Abstract

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 Natures 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.

Original languageEnglish
Pages (from-to)821-830
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume70
Issue number8
DOIs
Publication statusPublished - 2012 Dec 1

Keywords

  • Artificial oligonucleotide
  • Click chemistry
  • DNA
  • Primer
  • RNA
  • Reverse transcription

ASJC Scopus subject areas

  • Organic Chemistry

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