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

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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.

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

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Publication details

The article was received on 28 Jul 2017, accepted on 06 Sep 2017 and first published on 14 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB01874F
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Synthesis and thermal stabilities of oligonucleotides containing 2′-O,4′-C-methylene bridged nucleic acid with a phenoxazine base

    Y. Kishimoto, A. Fujii, O. Nakagawa, T. Nagata, T. Yokota, Y. Hari and S. Obika, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01874F

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