Directed crosslinking of RNA by glutathione‐triggered PNA‐quinone‐methide‐conjugates
- Quinone methide precursors protected with alkyldithiomethyl groups have been synthesized and converted into PNA conjugates. Stable in the absence of reducing agents, the electrophilic quinone methide is released by glutathione in concentrations typical for the cytosol. Self-alkylation then occurs or crosslinking of RNA when hybridized with complementary strands. Fastest reactions are seen for the sterically least hindered compound.
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| Author: | Jan‐Erik HornungGND, Timo WeinrichGND, Michael GöbelORCiDGND |
|---|---|
| URN: | urn:nbn:de:hebis:30:3-782965 |
| DOI: | https://doi.org/10.1002/ejoc.202200318 |
| ISSN: | 1099-0690 |
| Parent Title (English): | European journal of organic chemistry |
| Publisher: | Wiley-VCH Verl. |
| Place of publication: | Weinheim |
| Document Type: | Article |
| Language: | English |
| Date of Publication (online): | 2022/04/06 |
| Date of first Publication: | 2022/04/06 |
| Publishing Institution: | Universitätsbibliothek Johann Christian Senckenberg |
| Release Date: | 2023/10/12 |
| Tag: | Alkylation of RNA; Antisense agents; Disulfide bond; Glutathione; Peptide nucleic acids |
| Volume: | 2022 |
| Issue: | 33, art. e202200318 |
| Article Number: | e202200318 |
| Page Number: | 6 |
| First Page: | 1 |
| Last Page: | 5 |
| Note: | Open Access funding enabled and organized by Projekt DEAL. |
| HeBIS-PPN: | 516362429 |
| Institutes: | Biochemie, Chemie und Pharmazie |
| Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| 5 Naturwissenschaften und Mathematik / 57 Biowissenschaften; Biologie / 570 Biowissenschaften; Biologie | |
| Sammlungen: | Universitätspublikationen |
| Licence (German): |  Creative Commons - CC BY - Namensnennung 4.0 International |
