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http://dx.doi.org/10.18419/opus-13525
Autor(en): | Eyberg, Juri Ringenberg, Mark Richert, Clemens |
Titel: | Caging of a strongly pairing fluorescent thymidine analog with soft nucleophiles |
Erscheinungsdatum: | 2022 |
Dokumentart: | Zeitschriftenartikel |
Seiten: | 9 |
Erschienen in: | Chemistry - a European journal 29 (2023), No. e202203289 |
URI: | http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-ds-135449 http://elib.uni-stuttgart.de/handle/11682/13544 http://dx.doi.org/10.18419/opus-13525 |
ISSN: | 1521-3765 0947-6539 |
Zusammenfassung: | Controlling the pairing strength of nucleobases in DNA through reactions with compounds found inside the cell is a formidable challenge. Here we report how a thiazolyl substituent turns a strongly pairing ethynylpyridone C‐nucleoside into a reactive residue in oligonucleotides. The thiazolyl‐bearing pyridone reacts with soft nucleophiles, such as glutathione, but not with hard nucleophiles like hydroxide or carbonate. The addition products pair much more weakly with adenine in a complementary strand than the starting material, and also change their fluorescence. This makes oligonucleotides containing the new deoxynucleoside interesting for controlled release. Due to its reactivity toward N, P, S, and Se‐nucleophiles, and the visual signal accompanying chemical conversion, the fluorescent nucleotide reported here may also have applications in chemical biology, sensing and diagnostics. |
Enthalten in den Sammlungen: | 03 Fakultät Chemie |
Dateien zu dieser Ressource:
Datei | Beschreibung | Größe | Format | |
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CHEM_CHEM202203289.pdf | 4,79 MB | Adobe PDF | Öffnen/Anzeigen |
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