Alkylsulfanylphenyl derivatives of cytosine and 7-deazaadenine nucleosides, nucleotides and nucleoside triphosphates: synthesis, polymerase incorporation to DNA and electrochemical study |
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Authors: | Macíčková-Cahová Hana Pohl Radek Horáková Petra Havran Luděk Špaček Jan Fojta Miroslav Hocek Michal |
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Affiliation: | Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam. 2, 16610 Prague 6, Czech Republic. |
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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 formation of compact layers on the electrode. Modified nucleotides and DNA with incorporated benzyl‐ or tritylsulfanylphenyl moieties produced signals in [Co(NH3)6]3+ ammonium buffer, attributed to the Brdi?ka catalytic response, depending on the negative potential applied. Repeated constant current chronopotentiometric scans in this medium showed increased Brdi?ka catalytic response, which suggests the deprotection of the alkylsulfanyl derivatives to free thiols under the conditions. |
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Keywords: | DNA polymerases electrochemistry nucleosides nucleotides organosulfur compounds |
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