Base-pairing properties of 8-aza-7-deazaadenine linked via the 8-position to the DNA backbone

Autor(en): Seela, F
Zulauf, M
Debelak, H
Stichwörter: 2'-DEOXYISOGUANOSINE; BUILDING-BLOCKS; CHAIN ORIENTATION; Chemistry; Chemistry, Multidisciplinary; DUPLEX STABILIZATION; FACILE SYNTHESIS; GLYCOSYLATION; NUCLEOSIDES; OLIGODEOXYRIBONUCLEOTIDES; OLIGONUCLEOTIDES; SUGAR CONFORMATION
Erscheinungsdatum: 2000
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: HELVETICA CHIMICA ACTA
Volumen: 83
Ausgabe: 7
Startseite: 1437
Seitenende: 1453
Zusammenfassung: 
The base-pairing properties of oligonucleotides containing the unusual N-8-linked 8-aza-7-deazaadenine 2'-deoxyribonucleoside (2a) as well as its 7-bromo derivative 2b are described. The oligonucleotides were prepared by solid-phase synthesis employing phosphoramidite chemistry. Compound 2a forms a strong base pair with T-d for which a reverse Watson-Crick pair is suggested (Fig. 9). Compound 2a displays a lower N-glycosylic-bond stability than its Ng-nucleoside and shows strong stacking interactions when incorporated into oligonucleotides. The replacement of 2'-deoxyadenosine by 2a does not significantly influence the duplex stability. However, this behavior depends on the position of the incorporation.
ISSN: 0018019X
DOI: 10.1002/1522-2675(20000705)83:7<1437::AID-HLCA1437>3.0.CO;2-U

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