A Nucleobase-Discriminating Pyrrolo-dC Click Adduct Designed for DNA Fluorescence Mismatch Sensing

Autor(en): Ming, Xin
Seela, Frank
Stichwörter: 7-DEAZAPURINE; ANALOGS; BASE; BUBBLE; Chemistry; Chemistry, Multidisciplinary; click chemistry; CYCLOADDITION; deazapurines; DUPLEXES; fluorescence; NUCLEIC-ACID; NUCLEOSIDE; OLIGONUCLEOTIDES; PROBES; sensors
Erscheinungsdatum: 2012
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: CHEMISTRY-A EUROPEAN JOURNAL
Volumen: 18
Ausgabe: 31
Startseite: 9590
Seitenende: 9600
Zusammenfassung: 
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 (F=0.32), which is 10 times higher than those of 8-methylpyrrolo-dC (1?b, F=0.026) or the long linker derivative 4 (F=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.
ISSN: 09476539
DOI: 10.1002/chem.201103385

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