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Helix formation of oligodeoxyribonucleotides containing base-aromatic ring conjugates
Mio Kubota1, Momo Kosuge, Akira Ono
1Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University, Minami-ohsawa 1-1, Hachioji, Tokyo 192-0397, Japan.
Nucleic Acids Research. Supplement (2001)
|September 27, 2003
Summary
Novel nucleoside analogues containing pyrene groups were synthesized and added to oligodeoxyribonucleotides (ODNs). Pyrene-containing ODNs showed fluorescence that decreased upon forming duplexes with complementary strands, indicating structural changes.
Area of Science:
- Organic Chemistry
- Biochemistry
- Molecular Biology
Background:
- Nucleoside analogues are crucial in developing novel nucleic acid structures.
- Pyrene-based molecules offer unique photophysical properties for molecular probes.
- Oligodeoxyribonucleotides (ODNs) are key components in molecular biology and diagnostics.
Purpose of the Study:
- To synthesize novel nucleoside analogues incorporating pyrene moieties.
- To incorporate these modified nucleosides into oligodeoxyribonucleotides (ODNs).
- To investigate the photophysical properties of pyrene-containing ODNs and their behavior upon duplex formation.
Main Methods:
- Chemical synthesis of pyrene-containing nucleoside analogues.
- Incorporation of analogues into oligodeoxyribonucleotides (ODNs) via solid-phase synthesis.
- Spectroscopic analysis (fluorescence) of ODNs in single-stranded and duplex forms.
Main Results:
- Successful synthesis and incorporation of novel pyrene-containing nucleoside analogues into ODNs.
- ODNs with tandem pyrene residues at the 5'-end exhibited characteristic excimer fluorescence.
- Duplex formation with complementary strands led to a significant decrease in excimer fluorescence, suggesting conformational changes.
Conclusions:
- Novel pyrene-containing nucleoside analogues can be effectively incorporated into ODNs.
- The fluorescence properties of these modified ODNs are sensitive to their secondary structure.
- These findings open avenues for using pyrene-labeled ODNs as probes for nucleic acid interactions.