title: 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 formation of compact layers on the electrode. Modified nucleotides and DNA with incorporated benzyl- or tritylsulfanylphenyl moieties produced signals in [Co(NH(3))(6)](3+) ammonium buffer, attributed to the Brdička catalytic response, depending on the negative potential applied. Repeated constant current chronopotentiometric scans in this medium showed increased Brdička catalytic response, which suggests the deprotection of the alkylsulfanyl derivatives to free thiols under the conditions.
authors.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.
authors.forename: Hana
authors.initials: H
authors.lastname: Macíčková-Cahová
authors.forename: Radek
authors.initials: R
authors.lastname: Pohl
authors.forename: Petra
authors.initials: P
authors.lastname: Horáková
authors.forename: Luděk
authors.initials: L
authors.lastname: Havran
authors.forename: Jan
authors.initials: J
authors.lastname: Špaček
authors.forename: Miroslav
authors.initials: M
authors.lastname: Fojta
authors.forename: Michal
authors.initials: M
authors.lastname: Hocek
mesh_terms: D001483:Base Sequence; D003596:Cytosine / Q000737:chemistry*; D004259:DNA-Directed DNA Polymerase / Q000737:chemistry* / Q000378:metabolism; D004563:Electrochemistry; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry* / Q000378:metabolism*; D009711:Nucleotides / Q000737:chemistry* / Q000378:metabolism*; D011122:Polyphosphates / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D009705:Nucleosides; D009711:Nucleotides; D011122:Polyphosphates; D013438:Sulfhydryl Compounds; D003596:Cytosine; D004259:DNA-Directed DNA Polymerase; C005692:triphosphoric acid