Abstract
The stability of the PNA (peptide nucleic acid) thymine monomer ¿N-[2-(thymin-1-ylacetyl)]-N-(2-aminoaminoethyl)glycine¿ and those of various PNA oligomers (5-8-mers) have been measured at room temperature (20 degrees C) as a function of pH. The thymine monomer undergoes N-acyl transfer rearrangement with a half-life of 34 days at pH 11 as analyzed by 1H NMR; and two reactions, the N-acyl transfer and a sequential degradation, are found by HPLC analysis to occur at measurable rates for the oligomers at pH 9 or above. Dependent on the amino-terminal sequence, half-lives of 350 h to 163 days were found at pH 9. At pH 12 the half-lives ranged from 1.5 h to 21 days. The results are discussed in terms of PNA as a gene therapeutic drug as well as a possible prebiotic genetic material.
| Original language | English |
|---|---|
| Journal | New Journal of Chemistry |
| Volume | 22 |
| Pages (from-to) | 1055-9 |
| Number of pages | 5 |
| ISSN | 0398-9836 |
| Publication status | Published - 1998 |
Keywords
- Evolution, Chemical
- Hydrogen-Ion Concentration
- Isomerism
- Magnetic Resonance Spectroscopy
- Peptide Nucleic Acids/chemical synthesis
- Polymers/chemical synthesis
- Solutions
- Thymine/analogs & derivatives
- Water/chemistry