7-halogenated 7-deaza-2'-deoxyxanthine 2'-deoxyribonucleosides

Autor(en): Seela, F
Shaikh, K
Stichwörter: 7-DEAZA-2'-DEOXYXANTHOSINE; 7-IODO-2'-DEOXYTUBERCIDIN; Chemistry; Chemistry, Multidisciplinary; DERIVATIVES; DNA; MAJOR GROOVE; NUCLEOSIDES; OLIGONUCLEOTIDES; STABILITY; SUBSTITUENTS; SUGAR CONFORMATION
Erscheinungsdatum: 2004
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: HELVETICA CHIMICA ACTA
Volumen: 87
Ausgabe: 6
Startseite: 1325
Seitenende: 1332
Zusammenfassung: 
The synthesis of the 7-halogenated derivatives 1b (7-bromo) and le (7-iodo) of 7-deaza-2'-deoxyxanthosine (1a) is described. A partial Br --> I exchange was observed when the demethylation of 6-methoxy precursor compound 4b was performed with Me3SiCl/NaI. This reaction is circumvented by the nucleophilic displacement of the MeO group under strong alkaline conditions. The halogenated 7-deaza-2'-deoxyxanthosine derivatives We show a decreased S-conformer population of the sugar moiety compared to the nonhalogenated 1a. They are expected to form stronger triplexes when they replace 1a in the 1 (.) dA (.) dT base triplet.
ISSN: 0018019X
DOI: 10.1002/hlca.200490121

Show full item record

Page view(s)

3
Last Week
0
Last month
1
checked on Feb 27, 2024

Google ScholarTM

Check

Altmetric