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Synthesis, Base Pairing, and Fluorescence Properties of Oligonucleotides Containing 1 H ‐Pyrazolo[3,4‐ d ]pyrimidin‐6‐amine (8‐Aza‐7‐deazapurin‐2‐amine) as an Analogue of Purin‐2‐amine
Author(s) -
Seela Frank,
Becher Georg
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(20000510)83:5<928::aid-hlca928>3.0.co;2-5
Subject(s) - chemistry , phosphoramidite , amine gas treating , deoxyribonucleosides , oligonucleotide , fluorescence , nucleoside , dna , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , physics , quantum mechanics
The synthesis of the N 9 ‐ and N 8 ‐( β ‐ D ‐2′‐deoxyribonucleosides) 2 and 10 , respectively, of 8‐aza‐7‐deazapurin‐2‐amine (=1 H ‐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.