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 | Enthalten in: | HELVETICA CHIMICA ACTA | Band: | 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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geprüft am 07.06.2024