engleski

Fluorophore-tagged Nucleobase Derivatives

Novel 1, 4-disubstituted-1, 2, 3-triazole pyrimidines were synthesized applying the copper(I)-catalysed azide–alkyne cycloaddition (CuAAC). Beside intrinsically fluorescent triazole ring (well-known pharmacophore), various substituents (originating from different azide precursors) additionally enable a wide range of applications of new derivatives. For instance, 1, 2, 3-triazole ring can noncovalently interact with DNA/RNA by hydrogen bonding and aromatic stacking interactions and spectrophotometrically report on small structural differences of DNA as well as RNA secondary structure. Novel triazole-nucleobase derivatives were prepared as amino acids with both, N- and C- enabled coupling, which allows easy and versatile incorporation into large variety of novel oligopeptides for various applications. Furthermore, triazole-nucleobase was combined with phenanthridine, later added with the aim to increase DNA/RNA affinity and contribute to the spectrophotometric recognition, thus yielding dual-fluorescence reporter conjugate.

Nucleobases; Click Chemistry; Fluorescence Conjugates

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