Anthraquinone as a redox label for DNA: synthesis, enzymatic incorporation, and electrochemistry of anthraquinone-modified nucleosides, nucleotides, and DNA
Language English Country Germany Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
- MeSH
- Anthraquinones chemistry MeSH
- Staining and Labeling methods MeSH
- DNA-Directed DNA Polymerase chemistry metabolism MeSH
- DNA chemistry MeSH
- Electrochemistry MeSH
- Molecular Structure MeSH
- Nucleosides chemistry metabolism MeSH
- Nucleotides chemistry metabolism MeSH
- Oligonucleotides chemistry metabolism MeSH
- Oxidation-Reduction MeSH
- Base Sequence MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Anthraquinones MeSH
- DNA-Directed DNA Polymerase MeSH
- DNA MeSH
- Nucleosides MeSH
- Nucleotides MeSH
- Oligonucleotides MeSH
Modified 2'-deoxynucleosides and deoxynucleoside triphosphates (dNTPs) bearing anthraquinone (AQ) attached through an acetylene or propargylcarbamoyl linker at the 5-position of pyrimidine (C) or at the 7-position of 7-deazaadenine were prepared by Sonogashira cross-coupling of halogenated dNTPs with 2-ethynylanthraquinone or 2-(2-propynylcarbamoyl)anthraquinone. Polymerase incorporations of the AQ-labeled dNTPs into DNA by primer extension with KOD XL polymerase have been successfully developed. The electrochemical properties of the AQ-labeled nucleosides, nucleotides, and DNA were studied by cyclic and square-wave voltammetry, which show a distinct reversible couple of peaks around -0.4 V that make the AQ a suitable redox label for DNA.
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