Without internal affiliation

  • Author: Andersen, Nicolai Krog

    University of Southern Denmark, Denmark

  • Author: Døssing, Holger

    Unknown

  • Author: Jensen, Frank

    Aarhus University, Denmark

  • Author: Vester, Birte

    University of Southern Denmark, Denmark

  • Author: Nielsen, Poul

    University of Southern Denmark, Denmark

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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
Publication date2011
Volume76
Issue15
Pages6177-6187
ISSN0022-3263
DOIs
StatePublished
CitationsWeb of Science® Times Cited: 16
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