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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