Alkylsulfanylphenyl Derivatives of Cytosine and 7‐Deazaadenine Nucleosides, Nucleotides and Nucleoside Triphosphates: Synthesis, Polymerase Incorporation to DNA and Electrochemical Study
Abstract:Aqueous Suzuki-Miyaura cross-coupling reactions of halogenated nucleosides, nucleotides and nucleoside triphosphates derived from 5-iodocytosine and 7-iodo-7-deazaadenine with methyl-, benzyl- and tritylsufanylphenylboronic acids gave the corresponding alkylsulfanylphenyl derivatives of nucleosides and nucleotides. The modified nucleoside triphosphates were incorporated into DNA by primer extension by using Vent(exo-) polymerase. The electrochemical behaviour of the alkylsulfanylphenyl nucleosides indicated fo… Show more
“…Both the inherent electrochemistry of nucleic acids and the electrochemistry of additional DNA labels have been extensively used in diverse bioanalytical applications 4. We have previously developed several new redox labels, including ferrocene,5 aminophenyl and nitrophenyl,6 [Os(bpy) 3 ] (bpy=2,2′‐bipyridyl),7 tetrathiafulvalene,8 anthraquinone,9 alkylsulfanylphenyl,10 hydrazones,11 and so on, and by combining four different labels for the four nucleobases, established the first generation of multipotential redox coding7 of DNA and applied it in minisequencing. However, in this first generation of redox labeling, only one or two labels (one reducible and one oxidizable)6 were incorporated and detected in one DNA molecule.…”
Benzofurazane has been attached to nucleosides and dNTPs, either directly or through an acetylene linker, as a new redox label for electrochemical analysis of nucleotide sequences. Primer extension incorporation of the benzofurazane-modified dNTPs by polymerases has been developed for the construction of labeled oligonucleotide probes. In combination with nitrophenyl and aminophenyl labels, we have successfully developed a three-potential coding of DNA bases and have explored the relevant electrochemical potentials. The combination of benzofurazane and nitrophenyl reducible labels has proved to be excellent for ratiometric analysis of nucleotide sequences and is suitable for bioanalytical applications.
“…Both the inherent electrochemistry of nucleic acids and the electrochemistry of additional DNA labels have been extensively used in diverse bioanalytical applications 4. We have previously developed several new redox labels, including ferrocene,5 aminophenyl and nitrophenyl,6 [Os(bpy) 3 ] (bpy=2,2′‐bipyridyl),7 tetrathiafulvalene,8 anthraquinone,9 alkylsulfanylphenyl,10 hydrazones,11 and so on, and by combining four different labels for the four nucleobases, established the first generation of multipotential redox coding7 of DNA and applied it in minisequencing. However, in this first generation of redox labeling, only one or two labels (one reducible and one oxidizable)6 were incorporated and detected in one DNA molecule.…”
Benzofurazane has been attached to nucleosides and dNTPs, either directly or through an acetylene linker, as a new redox label for electrochemical analysis of nucleotide sequences. Primer extension incorporation of the benzofurazane-modified dNTPs by polymerases has been developed for the construction of labeled oligonucleotide probes. In combination with nitrophenyl and aminophenyl labels, we have successfully developed a three-potential coding of DNA bases and have explored the relevant electrochemical potentials. The combination of benzofurazane and nitrophenyl reducible labels has proved to be excellent for ratiometric analysis of nucleotide sequences and is suitable for bioanalytical applications.
“…1,2 Due to the potential utilization of aryl bromides and iodides in the synthesis of aryl esters, aryl olefins and other useful compounds and their wide applications in medicine and biochemitry, [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] bromination and iodination of aromatic compounds have been the subject of numerous studies. Recently, the oxidative halogenation of organic compounds by halides have emerged as an important alternative for the synthesis of such haloderivatives.…”
Bromination and iodination of the aromatic compounds have efficiently been carried out at room temperature and 70 o C, respectively, in short reaction times using orthoperiodic acid/sodium bromide (1:2) and orthoperiodic acid/sodium iodide (1:2) in water to prepare the corresponding halo compounds with excellent yields.
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