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Frank Jensen

Duplex and triplex formation of mixed pyrimidine oligonucleotides with stacking of phenyl-triazole moieties in the major groove

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  • Nicolai Krog Andersen
  • ,
  • Holger Balslev Døssing
  • ,
  • Frank Jensen
  • Birte Vester
  • ,
  • Poul Nielsen
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
Volume76
Issue15
Pages (from-to)6177-87
Number of pages11
ISSN0022-3263
DOIs
Publication statusPublished - 2011

    Research areas

  • Base Sequence, Circular Dichroism, DNA, Complementary, Deoxycytidine, Deoxyuridine, Models, Molecular, Molecular Structure, Nucleic Acid Conformation, Nucleosides, Nucleotides, Oligonucleotides, Pyrimidines, RNA, Complementary, Triazoles

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