Green-Light Activatable BODIPY and Coumarin 5'-Caps for Oligonucleotide Photocaging
- We synthesized two green-light activatable 5’-caps for oligonucleotides based on the BODIPY and coumarin scaffold. Both bear an alkyne functionality allowing their use in numerous biological applications. They were successfully incorporated in oligonucleotides via solid-phase synthesis. Copper-catalyzed alkyne-azide cycloaddition (CuAAC) using a bisazide photo-tether gave cyclic oligonucleotides that could be relinearized by activation with green light and were shown to exhibit high stability against exonucleases. Chemical ligation as another example for bioconjugation yielded oligonucleotides with an internal strand break site. Irradiation at 530 nm or 565 nm resulted in complete photolysis of both caging groups.
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| Author: | Janik Kaufmann, Patricia Müller, Eleni Andreadou, Alexander HeckelORCiDGND |
|---|---|
| URN: | urn:nbn:de:hebis:30:3-790972 |
| DOI: | https://doi.org/10.1002/chem.202200477 |
| ISSN: | 1521-3765 |
| Pubmed Id: | https://pubmed.ncbi.nlm.nih.gov/35420231 |
| Parent Title (English): | Chemistry – a European journal |
| Publisher: | Wiley-VCH |
| Place of publication: | Weinheim |
| Document Type: | Article |
| Language: | English |
| Date of Publication (online): | 2022/04/14 |
| Date of first Publication: | 2022/04/14 |
| Publishing Institution: | Universitätsbibliothek Johann Christian Senckenberg |
| Release Date: | 2023/10/18 |
| Tag: | bioconjugation; click chemistry; green gap; oligonucleotides; photo-tethering; photochemistry; photolabile protecting groups |
| Volume: | 28 |
| Issue: | 36, art. e202200477 |
| Article Number: | e202200477 |
| Page Number: | 7 |
| First Page: | 1 |
| Last Page: | 7 |
| Note: | This work was funded by the Deutsche Forschungsgemeinschaft (SFB 902). Open Access funding enabled and organized by Projekt DEAL. |
| HeBIS-PPN: | 516370944 |
| Institutes: | Biochemie, Chemie und Pharmazie |
| Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Sammlungen: | Universitätspublikationen |
| Licence (German): |  Creative Commons - CC BY - Namensnennung 4.0 International |
