Modified Nucleic Acids pp 221-248

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

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

Chapter

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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Copyright information

© Springer International Publishing Switzerland 2016

Authors and Affiliations

  • Shigeki Sasaki
    • 1
  • Yosuke Taniguchi
    • 1
  • Fumi Nagatsugi
    • 2
  1. 1.Graduate School of Pharmaceutical SciencesKyushu UniversityHigashi-kuJapan
  2. 2.Institute of Multidisciplinary Research for Advanced MaterialsTohoku UniversityAoba-kuJapan

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