Base-Pairing Properties of 8-Aza-7-deazaadenine Linked via the 8-Position to the DNA Backbone

✍ Scribed by Frank Seela; Matthias Zulauf; Harald Debelak

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: German
• Weight: 346 KB
• Volume: 83
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/1522-2675(20000705)83:7<1437::aid-hlca1437>3.0.co;2-u

✦ Synopsis

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 N 9 -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.