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Specific Recognition of Single Nucleotide by Alkylating Oligonucleotides and Sensing of 8-Oxoguanine

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Modified Nucleic Acids

Part of the book series: Nucleic Acids and Molecular Biology ((NUCLEIC,volume 31))

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Abstract

Gene expression is regulated by hierarchical mechanisms, for which not only the sequence but also the special structure of DNA and RNA play a vital role. This sophisticated systems also feature specific chemical modification of nucleotides as epigenetic gene regulations such as 5-methylation of cytosine. Meantime, endogenous and exogenous chemical species react with the nucleotides to have significant impact on the genetic function by causing mutations. Among mutations, a single nucleotide alteration is the most frequently found in the disease-relating genes. Therefore, for the diagnostic and therapeutic purposes, oligonucleotides are desired to discriminate a single nucleotide difference. However, because of non-covalent hybridization of the oligonucleotide with DNA and RNA, discrimination of a single nucleotide difference is not always easy. We have focused on selective alkylation as a reliable strategy for a single base recognition. Molecular design has been performed so that a non-covalent complex in a hybridized complex induces a selective reaction to the target base. On the other hand, guanine is the most susceptible base for oxidation to produce 8-oxoguanine which has a strong mutagenicity. 8-Oxoguanine formed in cells is regarded as a biomarker of oxidative stress of the cell, and a convenient sensing method is desired for diagnostic purposes. Also, determination of 8-oxo-2′-deoxyguanosine in DNA is important to reveal the oxidative damaged site in DNA. In this chapter, design concept and specific alkylating reactions will be introduced.

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Authors and Affiliations

  1. Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka, 812-8582, Japan

    Shigeki Sasaki & Yosuke Taniguchi

  2. Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai, 980-8577, Japan

    Fumi Nagatsugi

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  1. Shigeki Sasaki
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  2. Yosuke Taniguchi
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Correspondence to Shigeki Sasaki .

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Editors and Affiliations

  1. The Institute of Scientific and Industri, Osaka University, Ibaraki, Osaka, Japan

    Kazuhiko Nakatani

  2. University of California, San Diego, La Jolla, California, USA

    Yitzhak Tor

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Sasaki, S., Taniguchi, Y., Nagatsugi, F. (2016). Specific Recognition of Single Nucleotide by Alkylating Oligonucleotides and Sensing of 8-Oxoguanine. In: Nakatani, K., Tor, Y. (eds) Modified Nucleic Acids. Nucleic Acids and Molecular Biology, vol 31. Springer, Cham. https://doi.org/10.1007/978-3-319-27111-8_11

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