The influence of modified purine bases on the stability of parallel DNA

Autor(en): Seela, F
Wei, CF
Becher, G
Zulauf, M
Leonard, P
Stichwörter: Chemistry; Chemistry, Medicinal; Chemistry, Organic; DNA; DUPLEXES; ISOGUANINE; nucleic acids; nucleosides; OLIGONUCLEOTIDES; Pharmacology & Pharmacy; STRANDED DNA; substituents effects
Erscheinungsdatum: 2000
Herausgeber: PERGAMON-ELSEVIER SCIENCE LTD
Journal: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volumen: 10
Ausgabe: 3
Startseite: 289
Seitenende: 292
Zusammenfassung: 
The stability of the parallel-stranded (ps) DNA duplexes is increased when the dA-residues are replaced by the 7-substituted 7-deaza-2'-deoxyadenosine derivatives 3a,b or the dG-residues by the 8-aza-7-deazapurine 2'-deoxynucleosides 6 and 7a,b. Also the N-7-glycosylated adenine 5 forms stable base pairs in ps-DNA while it destabilizes oligonucleotide duplexes with antiparallel chain orientation. The presence of a 2-amino group as in compound 4b is critical for the DNA-structure, leading to a much greater destabilization of the ps-hybrids than of aps-DNA. (C) 2000 Elsevier Science Ltd. All rights reserved.
ISSN: 0960894X
DOI: 10.1016/S0960-894X(99)00679-4

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