2011
DOI: 10.1002/chem.201003496
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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

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Cited by 42 publications
(22 citation statements)
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“…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.…”
Section: Introductionmentioning
confidence: 99%
“…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.…”
Section: Introductionmentioning
confidence: 99%
“…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.…”
Section: Introductionmentioning
confidence: 99%
“…Found: C,59.41;H,5.05;N,12.34. (Macickova-Cahova et al, 2011) 163.3, 154.2, 140.1, 133.8, 128.0, 127.1, 123.3, 103.0, 87.3, 85.2, 70.1, 61.0, 45.4. ESI-MS (m/z) = 310 (M + + H + ).…”
Section: -(2-napthyl)-2 -Deoxycytidine (S6d)mentioning
confidence: 99%