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

Autor(en): Seela, F
Wei, CF
Stichwörter: Chemistry; Chemistry, Multidisciplinary; ENZYMATIC INCORPORATION; IDENTIFICATION; ISOCYTOSINE; ISOGUANINE; ISOGUANOSINE; QUARTETS; RESIDUES; STRANDED DNA; TAUTOMERISM; TETRAPLEX
Erscheinungsdatum: 1999
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: HELVETICA CHIMICA ACTA
Volumen: 82
Ausgabe: 5
Startseite: 726
Seitenende: 745
Zusammenfassung: 
Oligonucleotides with parallel (ps) or antiparallel (aps) chain orientation containing 7-deaza-2'-deoxyisoguanosine (1) or 2'-deoxyisoguanosine (2) were prepared. The phosphoramidite and phosphonate building blocks 3-6 were synthesized and used in solid-phase synthesis. The diphenylcarbamoyl (dpc) residue was used for the 2-oxo group protection and the isobutyryl (iBu = ib) residue fur the amino function. Hybridization experiments were performed with oligonucleotides containing 7-deazaisoguanine or isoguanine. Regarding 7-deazapurine-containing oligonucleotides, the 7-deazaisoguanine cytosine base pair was the strongest in ps-duplexes, while that of 7-deazaisoguanine.5-methylisocytosine was the most stable one in aps-DNA. Ambiguous base pairing of 7-deazaisoguanine with cytosine, 5-methylisocytosine, thymine, and guanine was observed in the case of aps-duplexes, whereas in ps-duplexes, the ambiguity was extended to adenine. The 7-deazaisoguanine-containing duplexes showed almost identical base-pair stabilities as those containing isoguanine. According to this, various base-pair motifs are proposed. The 7-deaza-2'-deoxyisoguanosine was found to be an effective substitute of 2'-deoxyisoguanosine.
ISSN: 0018019X
DOI: 10.1002/(SICI)1522-2675(19990505)82:5<726::AID-HLCA726>3.0.CO;2-K

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