1,8-Naphthyridin-2,7-(1,8H)-dione is an effective mimic of protonated cytosine in peptide nucleic acid triplex recognition systems
Research output: Contribution to journal › Journal article › Research › peer-review
A novel bicyclic mimic of protonated cytosine [1,8-naphthyridin-2,7-(1,8H)-dione, (K)] for Hoogsteen type triplex recognition of guanine has been designed for incorporation into peptide nucleic acids. Bis-PNA clamps with the K base incorporated in the Hoogsteen strand showed a significant stabilization of the triplexes at pH 7 as compared to similar triplexes with PNA oligomers containing either cytosine (6.7 degrees C per unit) or pseudoisocytosine (1.5 degrees C per unit). Cooperative stabilization was observed when the K units were placed in adjacent positions ( approximately 3 degrees C per unit).
Original language | English |
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Journal | Bioorganic & Medicinal Chemistry Letters |
Volume | 12 |
Issue number | 21 |
Pages (from-to) | 3121-3124 |
Number of pages | 4 |
ISSN | 0960-894X |
DOIs | |
Publication status | Published - 4 Nov 2002 |
- Bridged Bicyclo Compounds/chemical synthesis, Cytosine/chemistry, DNA/chemistry, Drug Stability, Guanine/chemistry, Hot Temperature, Hydrogen Bonding, Indicators and Reagents, Molecular Mimicry, Naphthyridines/chemical synthesis, Peptide Nucleic Acids/chemistry, Stereoisomerism
Research areas
ID: 139320