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Hydroxylamine, Oxime and Hydroxamic Acid Derivatives of Nucleic Acids

Hydroxylamines, Oximes and Hydroxamic Acids (2010)

  1. Naoshi Kojima,
  2. Yasuo Komatsu

Published Online: 15 SEP 2010

DOI: 10.1002/9780470682531.pat0514

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Kojima, N. and Komatsu, Y. 2010. Hydroxylamine, Oxime and Hydroxamic Acid Derivatives of Nucleic Acids. Patai's Chemistry of Functional Groups. .

Author Information

  1. Bioproduction Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), Sapporo, Japan

Publication History

  1. Published Online: 15 SEP 2010

Abstract

Hydroxylamines directly react with nucleobases in genomic DNA, and the damaged nucleobases induce genetic mutations by forming non-canonical base pairs with natural bases. In contrast, some nucleoside analogues containing hydroxylamine and its related derivatives are known to possess antiviral and anticancer activities by mimicking natural nucleosides. In addition, oligonucleotides with phosphate backbones modified with hydroxylamines show nuclease resistance required for oligonucleotide therapeutics.

This chapter provides the fundamental functions and the applications of hydroxylamine, oxime and hydroxamic acid groups on nucleic acids, consisting of four contents (1. Reactions of hydroxylamine and O-methylhydroxylamine with nucleobases, 2. Nucleoside and nucleotide analogues consisting of hydroxylamine, oxime and hydroxamic acid groups, 3. A series of oligonucleotides modified at backbone and sugar moieties with these functional groups, and 4. Application for the detection and quantification of DNA lesions by aminooxy probes). Novel nucleic acids will be developed by understanding potential functions of hydroxylamine and its related derivatives.

Keywords:

  • nucleic acid;
  • nucleoside;
  • nucleotide;
  • oligonucleotide;
  • nucleoside analog;
  • isoxazolidinyl;
  • isoxazolinyl;
  • mutagenicity;
  • DNA lesion;
  • abasic site