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Issue 42, 2016
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Copper-mediated arylsulfanylations and arylselanylations of pyrimidine or 7-deazapurine nucleosides and nucleotides

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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.

Graphical abstract: Copper-mediated arylsulfanylations and arylselanylations of pyrimidine or 7-deazapurine nucleosides and nucleotides

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Publication details

The article was received on 31 Aug 2016, accepted on 29 Sep 2016 and first published on 29 Sep 2016


Article type: Paper
DOI: 10.1039/C6OB01917J
Citation: Org. Biomol. Chem., 2016,14, 10018-10022
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    Copper-mediated arylsulfanylations and arylselanylations of pyrimidine or 7-deazapurine nucleosides and nucleotides

    F. Botha, M. Slavíčková, R. Pohl and M. Hocek, Org. Biomol. Chem., 2016, 14, 10018
    DOI: 10.1039/C6OB01917J

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