Efficient RNA-targeting by the introduction of aromatic stacking in the duplex major groove via 5-(1-phenyl-1,2,3-triazol-4-yl)-2'-deoxyuridines.
Three pyrimidine nucleosides with differently substituted phenyltriazoles attached to the 5-position were prepared by Cu(I)-assisted azide-alkyne cycloadditions (CuAAC) and incorporated into oligonucleotides. Efficient π-π-stacking between two or more phenyltriazoles in the major groove was found to increase the thermal stability of a DNA:RNA duplex significantly. The best stacking, and most stable duplex, was obtained by a sulfonamide substituted derivative.
Andersen
Nicolai Krog
NK
Nucleic Acid Center, Department of Physics and Chemistry, University of Southern Denmark, 5230 Odense M, Denmark.
Chandak
Navneet
N
Brulíková
Lucie
L
Kumar
Pawan
P
Jensen
Michael Dalager
MD
Jensen
Frank
F
Sharma
Pawan K
PK
Nielsen
Poul
P
D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D002942:Circular Dichroism; D003300:Copper / Q000737:chemistry; D004247:DNA / Q000737:chemistry; D003857:Deoxyuridine / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D008958:Models, Molecular; D009693:Nucleic Acid Hybridization; D012313:RNA / Q000737:chemistry*
D000480:Alkynes; D001386:Azides; D012313:RNA; D003300:Copper; D004247:DNA; D003857:Deoxyuridine