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Three-Component Bioorthogonal Reactions on Cellular DNA and RNA.
Journal article

Three-Component Bioorthogonal Reactions on Cellular DNA and RNA.

  • Tera M Department of Chemistry , University of Zurich , Winterthurerstrasse 190 , 8057 Zurich , Switzerland.
  • Luedtke NW Department of Chemistry , University of Zurich , Winterthurerstrasse 190 , 8057 Zurich , Switzerland.
  • 2019-11-08
Published in:
  • Bioconjugate chemistry. - 2019
Azides
Cross-Linking Reagents
DNA
Diynes
Fluorescent Dyes
Intercalating Agents
Molecular Imaging
RNA
English Metabolic incorporation of bioorthogonal functional groups into chromatin, followed by copper-free conjugation reactions, often gives low yields due to steric hindrance. Here we report that a cationic Sondheimer diyne derivative "DiMOC" rapidly reacts with azide groups in duplex DNA that are otherwise unreactive toward aliphatic cyclooctynes such as bicyclo[6.1.0]nonyne (BCN). DiMOC reversibly intercalates into duplex DNA and undergoes tandem strain-promoted cross-linking of two different azide groups to give DNA-DiMOC-"X" cross-links, where "X" theoretically represents a fluorescent probe, affinity tag, RNA, protein, carbohydrate, and so forth. As a proof of principle, the metabolic incorporation of azide-modified nucleosides into cellular DNA or RNA, followed by treatment with DiMOC and a fluorescent azide enabled visualization of newly synthesized nucleic acids in whole cells.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://sonar.ch/global/documents/164620
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