title: 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.
abstract: 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.
authors.affiliation: Nucleic Acid Center, Department of Physics and Chemistry, University of Southern Denmark, 5230 Odense M, Denmark.
authors.forename: Nicolai Krog
authors.initials: NK
authors.lastname: Andersen
authors.forename: Navneet
authors.initials: N
authors.lastname: Chandak
authors.forename: Lucie
authors.initials: L
authors.lastname: Brulíková
authors.forename: Pawan
authors.initials: P
authors.lastname: Kumar
authors.forename: Michael Dalager
authors.initials: MD
authors.lastname: Jensen
authors.forename: Frank
authors.initials: F
authors.lastname: Jensen
authors.forename: Pawan K
authors.initials: PK
authors.lastname: Sharma
authors.forename: Poul
authors.initials: P
authors.lastname: Nielsen
mesh_terms: 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*
chemical_list: D000480:Alkynes; D001386:Azides; D012313:RNA; D003300:Copper; D004247:DNA; D003857:Deoxyuridine