Acyclic artificial nucleic acids with phosphodiester bonds exhibit unique functions

DOI PDF Web Site 被引用文献3件 オープンアクセス

書誌事項

公開日
2016-04-20
権利情報
  • http://www.springer.com/tdm
  • http://www.springer.com/tdm
DOI
  • 10.1038/pj.2016.39
公開者
Springer Science and Business Media LLC

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説明

Artificial nucleic acids (XNAs) have potential as therapeutic agents and fluorescent probes. These acyclic nucleic acid mimics have several advantages, including facile chemical synthesis and resistance to nuclease-mediated cleavage. Here we review our recent progress on the preparation of acyclic XNAs. Acyclic D-threoninol nucleic acid (D-aTNA) forms an extremely stable homo-duplex with complementary D-aTNA, but D-aTNA does not form a stable duplex with either DNA or RNA. Serinol nucleic acid (SNA), which has nucleobases on a serinol backbone, forms stable hybrid helices with both DNA and RNA and has unique chiroptical properties. Both chirality and helicity of an SNA duplex depend on its sequence. L-aTNA, which is an enantiomer of D-aTNA, has the highest affinity for complementary DNA and RNA among these three XNAs. Attempts to apply these XNAs as drugs, fluorescent probes, and nanomaterials are underway. Although chemical differences among these XNAs are small, all have unique properties, and XNAs with different functional characteristics will be found by chemically modifying these XNAs. In this focus review, we overview our recent works on acyclic artificial nucleic acids (XNAs). Three acyclic XNAs, D-aTNA, SNA and L-aTNA have been developed. D-aTNA can form extremely stable homo-duplex, whereas it shows a high orthogonality with natural nucleic acids. SNA oligomers can change their helicity and chirality depending on sequences. L-aTNA can form stable duplexes with both DNA and RNA. Owing to unique properties of these XNAs, they should find application as tools in biology, biotechnology and nanotechnology.

収録刊行物

  • Polymer Journal

    Polymer Journal 48 (7), 781-786, 2016-04-20

    Springer Science and Business Media LLC

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