Synthesis and thermal stabilities of oligonucleotides containing 2′-O,4′-C-methylene bridged nucleic acid with a phenoxazine base

By Yuki Kishimoto, Akane Fujii, Osamu Nakagawa, Tetsuya Nagata, Takanori Yokota, Yoshiyuki Hari, Satoshi Obika

May 22, 2018

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Title

Synthesis and thermal stabilities of oligonucleotides containing 2′-O,4′-C-methylene bridged nucleic acid with a phenoxazine base

Author

Yuki Kishimoto, Akane Fujii, Osamu Nakagawa, Tetsuya Nagata, Takanori Yokota, Yoshiyuki Hari, Satoshi Obika

Year

2017

Journal

Organic & Biomolecular Chemistry

Abstract

We designed and synthesized a novel artificial 2′-O,4′-C-methylene bridged nucleic acid (2′,4′-BNA/LNA) with a phenoxazine nucleobase and named this compound BNAP. Oligodeoxynucleotide (ODN) containing BNAP showed higher binding affinities toward complementary DNA and RNA as compared to ODNs bearing 2′,4′-BNA/LNA with 5-methylcytosine or 2′-deoxyribonucleoside with phenoxazine. Thermodynamic analysis revealed that BNAP exhibits properties associated with the phenoxazine moiety in DNA/DNA duplexes and characteristics associated with the 2′,4′-BNA/LNA moiety in DNA/RNA duplexes.

Full Article

http://pubs.rsc.org/en/content/articlelanding/2017/ob/c7ob01874f

Instrument

J-720

Keywords

Circular dichroism, DNA structure, RNA structure, Biochemistry