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

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 st...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2000-02, Vol.10 (3), p.289-292
Main Authors: SEELA, F, CHANGFU WEI, BECHER, G, ZULAUF, M, LEONARD, P
Format: Article
Language:English
Subjects:
Analytical, structural and metabolic biochemistry
Base Sequence
Biological and medical sciences
Carbohydrates. Nucleosides and nucleotides
Chemistry
DNA - chemistry
Dna, deoxyribonucleoproteins
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
Nucleic Acid Conformation
Nucleic acids
Nucleosides, nucleotides and oligonucleotides
Organic chemistry
Preparations and properties
Purines - chemistry
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Summary: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.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(99)00679-4