Issue 42, 2016

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
31 Aug 2016
Accepted
29 Sep 2016
First published
29 Sep 2016
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2016,14, 10018-10022

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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