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Derivatization & Labeling of Nucleic Acids

Isabell Hellmuth

Functionalization of nucleosides, their subsequent phosphoramidite formation and introduction into DNA or RNA via automated solid phase oligo -nucleotide synthesis is of high importance in nucleic acid chemistry[5]. This strategy offers the opportunity to introduce new properties, as e.g. fluorescent probes, to the biopolymer. A common approach to attach these functional groups via C-C bond formation to the nucleobase, is to take advantage of transition metal catalyzed cross-coupling reactions. Here, we apply the Suzuki-Miyaura cross-coupling reaction[6] with a variety of functional arylboronic acids to 5-bromo-2’-deoxyuridine (BrdU), a synthetic analog of thymidine, and in parallel to BrdU containing DNA-oligonucleotides.

Nucleic acid modification for labeling via click chemistry

Olwen Domingo
The chemical modification and fluorescent labeling of siRNA contribute largely to the development of therapeutic agents in RNA interference. However, such labeling may alter the physicochemical properties, such as base pairing, of the native RNA. After chemically modifying RNA nucleobases, to allow the copper mediated click functionalization of siRNA, studies have been conducted to evaluate the influence of such labeling on RNA properties, e.g. the role of siRNA in the translation of the GFP reporter gene[7].