Ehrenschwender, Thomas and Wagenknecht, Hans-Achim (2008) Synthesis and Spectroscopic Characterization of BODIPY-Modified Uridines as Potential Fluorescent Probes for Nucleic Acids. SYNTHESIS-STUTTGART (22). pp. 3657-3662. ISSN 0039-7881, 1437-210X
Full text not available from this repository. (Request a copy)Abstract
BODIPY-modified nucleosides that contain the fluorophore attached to the 5-position of uridine via a short phenylene bridge have been prepared and characterized by optical spectroscopy and by electrochemistry. The target compounds were synthesized using a Pd-catalyzed cross-coupling of 4-formylphenylboronic acid to 5-iodo-2'-desoxyuridine, followed by acid-catalyzed formation of the BODIPY chromophore, The weakly electron-donating ethyl substituents in positions 2 and 6 of the BODIPY dye, shift both the absorption and emission properties of the corresponding modified uridines bathochromically and alter their redox properties. In contrast, exchange of the fluoro ligands at the boron center of the chromophores by methoxy groups does not change the optical properties but increases the electron-rich character of the BODIPY-modified uridines significantly.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PHOTOINDUCED ELECTRON-TRANSFER; REVERSIBLE TERMINATOR; COUPLING REACTIONS; ENERGY-TRANSFER; DNA; NUCLEOTIDE; DYES; OLIGONUCLEOTIDES; DERIVATIVES; ANALOGS; absorption; BODIPY; cyclic voltammetry; fluorescence; nucleoside |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Alumni or Retired Professors > Arbeitskreis Prof. Dr. Hans-Achim Wagenknecht Chemistry and Pharmacy > Institut für Organische Chemie > Alumni or Retired Professors |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 19 Oct 2020 05:47 |
| Last Modified: | 19 Oct 2020 05:47 |
| URI: | https://pred.uni-regensburg.de/id/eprint/30039 |
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