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Abstract We synthesized various C2-naphthylethynylated 8-aza-7-deaza-2′-deoxyadenosines 1a – 1c as novel environmentally sensitive fluorescent (ESF) purine nucleosides. In particular, the N,N -dimethylamino-substituted derivative 1c exhibits a remarkably high solvatochromicity (Δ… Click to show full abstract
Abstract We synthesized various C2-naphthylethynylated 8-aza-7-deaza-2′-deoxyadenosines 1a – 1c as novel environmentally sensitive fluorescent (ESF) purine nucleosides. In particular, the N,N -dimethylamino-substituted derivative 1c exhibits a remarkably high solvatochromicity (Δ λ = 111 nm). 1c -containing oligodeoxynucleotide (ODN) probes clearly discriminated an apurinic/apyrimidinic site (AP site) in the complementary strand via a change in emission wavelength and intensity when hybridized with a target ODN.
Journal Title: Tetrahedron Letters
Year Published: 2017
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