title: A nucleobase-discriminating pyrrolo-dC click adduct designed for DNA fluorescence mismatch sensing.
abstract: New pyrrolo-dC click adducts (4 and 5) tethered with a 1,2,3-triazole skeleton were synthesized and oligonucleotides were prepared. The triazole system was either directly linked to the pyrrolo moiety (5) or connected via an n-butyl linker (4). The quantum yield of nucleoside 5 (Φ=0.32), which is 10 times higher than those of 8-methylpyrrolo-dC (1 b, Φ=0.026) or the long linker derivative 4 (Φ=0.03), is maintained in oligonucleotides. Compound 5 was used as a nucleobase-discriminating fluorescence sensor in duplex DNA. Excellent mismatch discrimination was observed when 5 was positioned opposite the four canonical nucleosides. Compound 5 has the potential to be used for SNP detection in long DNA targets when conventional techniques such as high resolution melt analysis fail.
authors: Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstraße 11, 48149 Münster, Germany.
authors: Xin
authors: X
authors: Ming
authors: Frank
authors: F
authors: Seela
mesh_terms: D057930:Click Chemistry; D004247:DNA / Q000737:chemistry*; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005453:Fluorescence; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009705:Nucleosides; D011758:Pyrroles; C540526:pyrrolo-deoxycytidine; D003841:Deoxycytidine; D004247:DNA