8-Aza-2 `-deoxyguanosine: Base pairing, mismatch discrimination and nucleobase anion fluorescence sensing in single-stranded and duplex DNA

Autor(en): Seela, Frank
Jiang, Dawei
Xu, Kuiying
Stichwörter: 2-AMINOPURINE; 8-AZAPURINES; ANALOGS; BENZOTRIAZOLE; Chemistry; Chemistry, Organic; EMISSION PROPERTIES; GUANOSINE; NUCLEOSIDE; OLIGODEOXYNUCLEOTIDES; PYRROLO-C
Erscheinungsdatum: 2009
Herausgeber: ROYAL SOC CHEMISTRY
Journal: ORGANIC & BIOMOLECULAR CHEMISTRY
Volumen: 7
Ausgabe: 17
Startseite: 3463
Seitenende: 3473
Zusammenfassung: 
Oligodeoxyribonucleotides containing 8-aza-2'-deoxyguanosine 9 were synthesized and a new phosphoramidite 11, showing a high coupling yield in solid-phase synthesis, was prepared. Nucleoside 9 was found to be a perfect shape mimic of dG; it forms a strong base pair with dC and shows an excellent mismatch discrimination. Nucleoside 9 appears strongly fluorescent as the anion, and thus, it has unique reporter group properties as a replacement for dG. The pK(a)-value of 9 (8.4) is lower than that of dG (9.3) and increases from the single-stranded DNA (8.8) to duplex DNA (9.1). The fluorescence of the nucleoside 9 anion is decreased in ss-oligonucleotides and further reduced in duplex DNA. When mismatches of 9 are formed with the four DNA canonical bases, the fluorescence of mismatches is significantly higher than that of the perfectly paired duplex. The fluorescence of the nucleoside 9 anion correlates with the base pair stability.
ISSN: 14770520
DOI: 10.1039/b908017a

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