7-deazapurine oligodeoxyribonucleotides: The effects of 7-deaza-8-methylguanine on DNA structure and stability

Autor(en): Seela, F
Chen, YM
Mittelbach, C
Stichwörter: BASE; CD; Chemistry; Chemistry, Multidisciplinary; CONFORMATIONS; CRYSTAL; DUPLEX STABILITY; OLIGONUCLEOTIDES; RESIDUES; SEQUENCES; TETRAPLEX
Erscheinungsdatum: 1998
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: HELVETICA CHIMICA ACTA
Volumen: 81
Ausgabe: 3
Startseite: 570
Seitenende: 583
Zusammenfassung: 
Oligodeoxyribonucleotides containing 7-deaza-2'droxy-8-methylguanosine (m(8)c(7)G(d); 2b) were prepared. For this purpose, the phosphonate 3a and the phosphoramidite 3b were synthesized and employed in solid-phase oligodeoxyribonucleotide synthesis. The structures and the thermodynamic data of duplex formation of oligodeoxyribonucleotides containing 2b were investigated by temperature-dependent CD and UV spectra and compared with those containing 7-deaza-2'-deoxy-7-methylguanosine (m(7)c(7)G(d)) or 7-deaza-2'-deoxyguanosine (c(7)G(d); 2a). In general, compound 2b reduces the duplex stability. In case of the sequence d(m(8)c(7)G-C)(4) (18), the B --> Z transition was Facilitated by the incorporation of 2b. Moreover, a single 7-deaza-8-methylguanine residue present in an oligodeoxyribonucleotide tract of guanine residues destabilizes the dG quadruplex significantly. This destabilization is more pronounced than in the case of 7-deazaguanine or 7-deaza-7-methylguanine.
ISSN: 0018019X
DOI: 10.1002/hlca.19980810310

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