About: Alkylsulfanylphenyl derivatives of cytosine and 7-deazaadenine nucleosides, nucleotides and nucleoside triphosphates. Synthesis, polymerase incorporation to DNA and electrochemical study     Goto   Sponge   NotDistinct   Permalink

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  • Aqueous Suzuki-Miyaura cross-coupling reactions of halogenated nucleosides, nucleotides and nucleoside triphosphates (dNTPs) 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 dNTPs were incorporated to DNA by primer extension using Vent(exo-) polymerase. Electrochemical behaviour of the alkyl-sulfanylphenyl nucleosides indicated formation of compact layers on the electrode. Modified nucleotides and DNA bearing benzyl- or tritylsulfanylphenyl moieties produced signals in [Co(NH3)6]3+ ammonium buffer attributable to the Brdicka catalytic reponses (BCR), depending on negative potential applied. Repeated potential scans in this medium of constant current chronopotentiometric showed increased BCR suggesting the deprotection of the alkylsulfanyl derivatives to free thiols under those conditions.
  • Aqueous Suzuki-Miyaura cross-coupling reactions of halogenated nucleosides, nucleotides and nucleoside triphosphates (dNTPs) 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 dNTPs were incorporated to DNA by primer extension using Vent(exo-) polymerase. Electrochemical behaviour of the alkyl-sulfanylphenyl nucleosides indicated formation of compact layers on the electrode. Modified nucleotides and DNA bearing benzyl- or tritylsulfanylphenyl moieties produced signals in [Co(NH3)6]3+ ammonium buffer attributable to the Brdicka catalytic reponses (BCR), depending on negative potential applied. Repeated potential scans in this medium of constant current chronopotentiometric showed increased BCR suggesting the deprotection of the alkylsulfanyl derivatives to free thiols under those conditions. (en)
Title
  • Alkylsulfanylphenyl derivatives of cytosine and 7-deazaadenine nucleosides, nucleotides and nucleoside triphosphates. Synthesis, polymerase incorporation to DNA and electrochemical study
  • Alkylsulfanylphenyl derivatives of cytosine and 7-deazaadenine nucleosides, nucleotides and nucleoside triphosphates. Synthesis, polymerase incorporation to DNA and electrochemical study (en)
skos:prefLabel
  • Alkylsulfanylphenyl derivatives of cytosine and 7-deazaadenine nucleosides, nucleotides and nucleoside triphosphates. Synthesis, polymerase incorporation to DNA and electrochemical study
  • Alkylsulfanylphenyl derivatives of cytosine and 7-deazaadenine nucleosides, nucleotides and nucleoside triphosphates. Synthesis, polymerase incorporation to DNA and electrochemical study (en)
skos:notation
  • RIV/68081707:_____/11:00360998!RIV12-AV0-68081707
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  • P(GA203/09/0317), P(IAA400040901), P(LC06035), P(LC512), Z(AV0Z40550506), Z(AV0Z50040507), Z(AV0Z50040702)
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  • 21
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  • 185217
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  • RIV/68081707:_____/11:00360998
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  • DNA polymerases; electrochemistry; nucleosides; nucleotides; organosulfur compounds (en)
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  • DE - Spolková republika Německo
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  • [9F287B7B8D69]
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  • Chemistry - A European Journal
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  • 17
http://linked.open...iv/tvurceVysledku
  • Fojta, Miroslav
  • Havran, Luděk
  • Hocek, Michal
  • Horáková, Petra
  • Macíčková-Cahová, Hana
  • Pohl, Radek
  • Špaček, Jan
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  • 000291594800011
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issn
  • 0947-6539
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  • 10.1002/chem.201003496
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