Designing new isomorphic fluorescent nucleobase analogues: the thieno[3,2-d]pyrimidine core

Fluorescent Analogs of Biomolecular Building Blocks: Design, Properties, and Applications

“…The [3,2] isomeric nucleosides, prepared as both a pyrimidine and purine analog ( N -nucleoside 6.161/162 and C -nucleoside 6.163 , respectively), show an absorption at ∼ 290 nm with a corresponding weak emission centered at ∼350 nm (Φ = 0.02 – 0.058) 598. In contrast, the isomeric [3,4] analog ( 6.164 ), while displaying a similar absorption band (304 nm), gives rise to a strong and red shifted visible emission (412 nm, Φ = 0.48) 597.…”

Strain Promoted Click Chemistry of 8-Azidopurine and 5-Azidopyrimidine Nucleosides and Nucleotides with Cyclooctynes and Applications to Living Cell Imaging

“…181,197 The 2-aminopurine 156, is possibly the most widely recognized fluorescent nucleoside, is an emissive isosteric adenosine analogue 198 and has been used extensively in biochemical studies and assay development. [199][200] Variations of 156, including modified 7-deaza and 8-aza-7-deaza analogues have been studied by Seela and coworkers as click chemistry substrates.…”

Labeling Oligonucleotides toward the Biomedical Probe

“…The natural purine and pyrimidine nucleobases have poor fluorescent properties, and thus they cannot be introduced into sequence probing systems. Recently, there have been diverse efforts to design modified nucleosides containing expanded nucleobases and conjugated nucleobase analogues [112]. Kim and coworkers proposed the QF-MB system containing fluorescent nucleoside Fl U at the middle loop of the hairpin DNA (Figure 8.17) [113].…”