Varghese, Reji and Gajula, Praveen Kumar and Chakraborty, Tushar Kanti and Wagenknecht, Hans-Achim (2009) Thieme Chemistry Journal Awardees - Where Are They Now? Synthesis and Optical Properties of Nile Red Modified 2 '-Deoxyuridine and 7-Deaza-2 '-deoxyadenosine: Highly Emissive Solvatochromic Nucleosides. SYNLETT (20). pp. 3252-3257. ISSN 0936-5214, 1437-2096
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A general synthetic strategy for the attachment of Nile red through a rigid acetylene linker to 2'-deoxyuridine and 7-deaza-2'-deoxyadenosine using Sonogashira coupling is demonstrated. Protection of either 5'-OH or N-7 of the nucleosides increased the yields of the cross-couplings significantly. Both Nile red modified 2'-deoxyuridine and 7-deaza-2'-deoxyadenosine as well as their derivatives exhibit excellent fluorescence quantum efficiencies and positive solvatochromism. The incorporation of the Nile red modified 2'-deoxyuridine into oligonucleotides yields bright fluorescent probes with maintained canonical base pairing in DNA.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | MOLECULAR BEACONS; ENERGY-TRANSFER; SUPRAMOLECULAR SCAFFOLD; OLIGONUCLEOTIDE PROBES; ELECTRON-TRANSFER; DNA; FLUORESCENT; STRATEGY; DESIGN; ZEOLITES; cross-coupling; dyes; nucleosides; solvent effects; spectroscopy |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Alumni or Retired Professors > Arbeitskreis Prof. Dr. Hans-Achim Wagenknecht |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 31 Aug 2020 12:54 |
| Last Modified: | 31 Aug 2020 12:54 |
| URI: | https://pred.uni-regensburg.de/id/eprint/28095 |
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