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

Autor(en): Seela, F
Becher, G
Stichwörter: 2-AMINOPURINE; Chemistry; Chemistry, Multidisciplinary; CONFORMATION; CYTOSINE; DNA; NMR; NUCLEOSIDES; OLIGODEOXYRIBONUCLEOTIDES; OLIGOMER; PYRAZOLO<3,4-D>PYRIMIDINES
Erscheinungsdatum: 2000
Herausgeber: WILEY-BLACKWELL
Journal: HELVETICA CHIMICA ACTA
Volumen: 83
Ausgabe: 5
Startseite: 928
Seitenende: 942
Zusammenfassung: 
The synthesis of the N(9)- and N(R)-(beta-D-2'-deoxyribonucleosides) 2 and 10. respectively, of 8-aza-7-deazapurin-2-amine (= 1 H-pyrazolo[3.4-d] rimiclin-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 phosphormidite 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 save T(m) values similar lu those determined from the UV melting curves.
ISSN: 0018019X
DOI: 10.1002/(SICI)1522-2675(20000510)83:5<928::AID-HLCA928>3.0.CO;2-5

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