Pyrazolo[3,4-d][1,2,3]triazine DNA: Synthesis and base pairing of 7-deaza-2,8-diaza-2 `-deoxyadenosine

Autor(en): Seela, F
Lindner, M
Glacon, V
Lin, WQ
Stichwörter: 2',3'-DIDEOXYRIBONUCLEOSIDES; 2'-DEOXYRIBOFURANOSIDES; ANALOGS; Chemistry; Chemistry, Organic; DERIVATIVES; GLYCOSYLATION; IMIDAZOLE NUCLEOSIDES; NUCLEOBASE-ANION; OLIGONUCLEOTIDES; PURINE; STABILITY
Erscheinungsdatum: 2004
Herausgeber: AMER CHEMICAL SOC
Journal: JOURNAL OF ORGANIC CHEMISTRY
Volumen: 69
Ausgabe: 14
Startseite: 4695
Seitenende: 4700
Zusammenfassung: 
7-Deaza-2,8-diaza-2'-deoxyadenosine (4) was synthesized from 8-aza-7-deaza-2'-deoxyadenosine (1) via the 1,N-6-etheno derivative 5. Ring opening with sodium hydroxide followed by ring closure in the presence of sodium nitrite formed the tricyclic intermediate 5 from which the transiently introduced ``etheno'' moiety was removed with NBS. Compound 4 was converted to the phosphoramidite 11, which was employed in solid-phase oligonucleotide synthesis. Base pairing studies on 4, incorporated in a 12-mer duplex, showed that this adenine nucleoside analogue forms a strong base pair with dG but not with dT. This novel base pair is as stable as that of the canonical dA-dT pair. As a result of the absence of nitrogen-7 compound 4 is expected to form a face to face base pair with dG.
ISSN: 00223263
DOI: 10.1021/jo040150i

Show full item record

Page view(s)

2
Last Week
0
Last month
0
checked on Feb 28, 2024

Google ScholarTM

Check

Altmetric