Surprising duplex stabilisation upon mismatch introduction within triply modified duplexes.
Three different modified phosphoramidite nucleoside building blocks equipped with additional protected imidazole, masked alcohol and masked carboxylate functionality are synthesized and incorporated into oligonucleotides. Based on the serine-protease active site model, doubly and triply modified duplexes are created and tested for stability. Analysis of different spatial distributions of the extra functionalities shows that careful positioning can even overcome duplex destabilisation caused by the introduction of mismatches.
Ghent University, Department of Organic Chemistry, Krijgslaan, Belgium.
Mieke A
MA
Catry
Vicky
V
Gheerardijn
Annemieke
A
Madder
D020137:Base Pair Mismatch; D001483:Base Sequence; D020134:Catalytic Domain; D004247:DNA / Q000737:chemistry*; D021881:DNA, Catalytic / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000737:chemistry; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry; D057057:Serine Proteases / Q000737:chemistry
D021881:DNA, Catalytic; D007093:Imidazoles; D009705:Nucleosides; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D004247:DNA; D057057:Serine Proteases