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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geprüft am 17.05.2024