Without internal affiliation

  • Author: Andersen, Nicolai Krog

    University of Southern Denmark, Denmark

  • Author: Døssing, Holger


  • Author: Jensen, Frank

    Aarhus University, Denmark

  • Author: Vester, Birte

    University of Southern Denmark, Denmark

  • Author: Nielsen, Poul

    University of Southern Denmark, Denmark

View graph of relations

5-(1-Phenyl-1,2,3-triazol-4-yl)-2′-deoxycytidine was synthesized from a modified CuAAC protocol and incorporated into mixed pyrimidine oligonucleotide sequences together with the corresponding 5-(1-phenyl-1,2,3-triazol-4-yl)-2′-deoxyuridine. With consecutive incorporations of the two modified nucleosides, improved duplex formation with a complementary RNA and improved triplex formation with a complementary DNA duplex were observed. The improvement is due to π–π stacking of the phenyl-triazole moieties in the major groove. The strongest stacking and most pronounced positive influence on thermal stability was found in between the uridine analogues or with the cytidine analogue placed in the 3′ direction to the uridine analogue. Modeling indicated a different orientation of the phenyl-triazole moieties in the major groove to account for the difference between the two nucleotides. The modified oligonucleotides were all found to be significantly stabilized toward nucleolytic degration.
Original languageEnglish
JournalJournal of Organic Chemistry
Issue number15
Pages (from-to)6177-6187
StatePublished - 2011
CitationsWeb of Science® Times Cited: 18
Download as:
Download as PDF
Select render style:
Download as HTML
Select render style:
Download as Word
Select render style:

ID: 35964184