Abstract
We synthesized 16 pyrrolidine-based oxy-peptide nucleic acid (POPNA) monomers carrying four different nucleobases onto four different stereoisomers of pyrrolidine rings. Using these monomers, we prepared POPNA oligomers, which formed sequence-specific hybrids with DNAs. The oligomer configurations influenced the hybrid stability. The oligomers were not taken into CHO cells. However, they could enter the cell cytoplasm when mixed with the influenza virus hemagglutinin peptide-arginine heptamer conjugate.
| Original language | English |
|---|---|
| Pages (from-to) | 9659-9666 |
| Number of pages | 8 |
| Journal | Tetrahedron |
| Volume | 66 |
| Issue number | 51 |
| DOIs | |
| Publication status | Published - Dec 18 2010 |
Keywords
- Cell-penetrating peptide
- Confocal laser scanning microscopy
- Peptide nucleic acid
- Solid-phase peptide synthesis
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Cite this
Kitamatsu, M., Takahashi, A., Ohtsuki, T., & Sisido, M. (2010). Synthesis of pyrrolidine-based oxy-peptide nucleic acids carrying four types of nucleobases and their transport into cytoplasm. Tetrahedron, 66(51), 9659-9666. https://doi.org/10.1016/j.tet.2010.10.056