Quinazoline-2,4(1H,3H)-dione as a substitute for thymine in triple- helix forming oligonucleotides: a reassessment
| Autor: | Joseph Vercauteren, Serge Moreau, Jean-Jacques Toulmé, Justine Michel |
|---|---|
| Rok vydání: | 1996 |
| Předmět: |
Phosphoramidite
Hot Temperature Magnetic Resonance Spectroscopy Molecular Structure Pyrimidine Oligonucleotide Stereochemistry Oligonucleotides Biology Nucleic Acid Denaturation Thymine chemistry.chemical_compound Drug Stability chemistry Biochemistry Quinazolines Genetics Quinazoline Nucleic Acid Conformation Nucleoside Q Research Article Triple helix |
| Zdroj: | Nucleic Acids Research. 24:1127-1135 |
| ISSN: | 1362-4962 |
| Popis: | A major limitation in triple-helix formation arises from the weak energy of interaction between the third strand and the double-stranded target. We tried to increase the stacking interaction contribution within the third strand by extending the aromatic domain of thymine. We report here the use of 2,4-quinazolinedione as a substitute for thymine in the canonical TA*T triplet. The synthesis and the characterization of the quinazoline beta nucleoside Q and of its phosphoramidite derivative is described. Triple-helix- forming oligonucleotides incorporating Q have been prepared and their ability to form triplexes has been evaluated by UV-monitored thermal denaturation measurements. The introduction of one or multiple Q residues, either contiguous or remote from each other, slightly destabilized triple-stranded structures, whatever the nucleic acid base composition (pyrimidine or GT) of the third strand. |
| Databáze: | OpenAIRE |
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