109737-96-4Relevant articles and documents
Synthesis, base pairing, and fluorescence properties of oligonucleotides containing 1H-pyrazolo[3,4-d]pyrimidin-6-amine (8-aza-7-deazapurin-2-amine) as an analogue of purin-2-amine
Seela, Frank,Becher, Georg
, p. 928 - 942 (2007/10/03)
The synthesis of the N9- and N8-(β-D-2'-deoxyribonucleosides) 2 and 10, respectively, of 8-aza-7-deazapurin-2-amine (=1H-pyrazolo[3,4- d]pyrimidin-6-amine) is described. The fluorescence properties and the stability of the N-glycosylic bond of 2 were determined and compared with those of the 2'-deoxyribonucleosides 1 and 3 of purin-2-amine and 7- deazapurin-2-amine respectively. From the nucleoside 2, the phosphoramidite 14 was prepared, and oligonucleotides were synthesized. Duplexes containing compound 1 or 2 are slightly less stable than those containing 2'- deoxyadenosine, while their CD spectra are rather different. The fluorescence of the nucleosides is strongly quenched (>95%) in single-stranded as well as in duplex DNA. The residual fluorescence was used to determine the melting profiles, which gave T(m) values similar to those determined from the UV melting curves.