The base pairing properties of 8-aza-7-deaza-2 `, deoxyisoguanosine and 7-halogenated derivatives in oligonucleotide duplexes with parallel and antiparallel chain orientation

Autor(en): Seela, F
Kroschel, R
Stichwörter: 2'-DEOXYISOGUANOSINE; 2-DIMENSIONAL NMR; ANALOGS; Biochemistry & Molecular Biology; ISOCYTOSINE; ISOGUANINE-CYTOSINE; OLIGODEOXYNUCLEOTIDES; RESIDUES; STABILITY; STRANDED DNA
Erscheinungsdatum: 2003
Herausgeber: OXFORD UNIV PRESS
Journal: NUCLEIC ACIDS RESEARCH
Volumen: 31
Ausgabe: 24
Startseite: 7150
Seitenende: 7158
Zusammenfassung: 
The base pairing properties of oligonucleotide duplexes containing 8-aza-7-deaza-2'-deoxyisoguanosine, its 7-bromo or its 7-lodo derivative are described. The nucleosides were synthesized on a convergent route, protected and converted into phosphoramidites. Oligonucleotides were prepared on a solid-phase and were hybridized to yield duplexes with parallel (ps) or antiparallel (aps) chain orientation. The 8-aza-7-deaza-2'-deoxyisoguanosine-containing duplexes show almost identical base pairing stability as those containing 2'-deoxyisoguanosine, while the 7-substituted derivatives induce a significant duplex stabilization both in ps and aps DNA. Self-complementary duplexes with parallel chain orientation are exceptionally stable due to the presence of 5'-overhangs. The bulky halogen substituents were found to be well accommodated in the grooves both of aps and ps DNA.
ISSN: 03051048
DOI: 10.1093/nar/gkg926

Show full item record

Google ScholarTM

Check

Altmetric