Fuechtbauer, Anders F.; Wranne, Moa S.; Sarangamath, Sangamesh; Bood, Mattias; El-Sagheer, Afaf H.; Brown, Tom; Graden, Henrik; Grotli, Morten; Wilhelmsson, L. Marcus published the artcile< Lighting Up DNA with the Environment-Sensitive Bright Adenine Analogue qAN4>, Category: imidazoles-derivatives, the main research area is qAN4 DNA oligonucleotide solid phase synthesis photophys property; DNA; FRET; base pairing; nucleobase analogues; photophysics.
The fluorescent adenine analog qAN4 was recently shown to possess promising photophys. properties, including a high brightness as a monomer. Here we report the synthesis of the phosphoramidite of qAN4 and its successful incorporation into DNA oligonucleotides using standard solid-phase synthesis. CD and thermal melting studies indicate that the qAN4-modification has a stabilizing effect on the B-form of DNA. Moreover, qAN4 base-pairs selectively with thymine with mismatch penalties similar to those of mismatches of adenine. The low energy absorption band of qAN4 inside DNA has its peak around 358 nm and the emission in duplex DNA is partly quenched and blue-shifted (ca. 410 nm), compared to the monomeric form. The spectral properties of the fluorophore also show sensitivity to pH; a property that may find biol. applications. Quantum yields in single-stranded DNA range from 1-29 % and in duplex DNA from 1-7 %. In combination with the absorptive properties, this gives an average brightness inside duplex DNA of 275 M-1 cm-1, more than five times higher than the most used environment-sensitive fluorescent base analog, 2-aminopurine. Finally, we show that qAN4 can be used to advantage as a donor for interbase FRET applications in combination with adenine analog qAnitro as an acceptor.
ChemPlusChem published new progress about Circular dichroism. 452-06-2 belongs to class imidazoles-derivatives, and the molecular formula is C5H5N5, Category: imidazoles-derivatives.
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem