title: Copper-mediated arylsulfanylations and arylselanylations of pyrimidine or 7-deazapurine nucleosides and nucleotides.
abstract: The syntheses of 5-arylsulfanyl- or 5-arylselanylpyrimidine and 7-arylsulfanyl- or 7-arylselanyl-7-deazapurine nucleosides and nucleotides were developed by the Cu-mediated sulfanylations or selanylations of the corresponding 5-iodopyrimidine or 7-iodo-7-deazapurine nucleosides or nucleotides with diaryldisulfides or -diselenides. The reactions were also applicable for direct modifications of 2'-deoxycytidine triphosphate and the resulting 5-arylsulfanyl or 5-arylselanyl-dCTP served as substrates for the polymerase synthesis of modified DNA bearing arylsulfanyl or arylselanyl groups in the major groove.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Science Czech Republic, Gilead Sciences and IOCB Research Center, Flemingovo nám. 2, 16610 Prague 6, Czech Republic. hocek@uochb.cas.cz.
authors.forename: Filip
authors.initials: F
authors.lastname: Botha
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Science Czech Republic, Gilead Sciences and IOCB Research Center, Flemingovo nám. 2, 16610 Prague 6, Czech Republic. hocek@uochb.cas.cz.
authors.forename: Michaela
authors.initials: M
authors.lastname: Slavíčková
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Science Czech Republic, Gilead Sciences and IOCB Research Center, Flemingovo nám. 2, 16610 Prague 6, Czech Republic. hocek@uochb.cas.cz.
authors.forename: Radek
authors.initials: R
authors.lastname: Pohl
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Science Czech Republic, Gilead Sciences and IOCB Research Center, Flemingovo nám. 2, 16610 Prague 6, Czech Republic. hocek@uochb.cas.cz and Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 12843 Prague 2, Czech Republic.
authors.forename: Michal
authors.identifier: http://orcid.org/0000-0002-1113-2047
authors.initials: M
authors.lastname: Hocek
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D011687:Purines / Q000737:chemistry*; D011742:Pyrimidine Nucleotides / Q000737:chemistry*
chemical_list: C512929:7-deazapurine; D011687:Purines; D011742:Pyrimidine Nucleotides; D003300:Copper