Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 5, Pages 1912-1916Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201508893
Keywords
DNA; epigenetics; fluorogenic probes; modified nucleobases; RNA
Categories
Funding
- Cluster of Excellence
- DFG Research Center Nanoscale Microscopy and Molecular Physiology of the Brain (CNMPB)
- DFG Priority Program Chemical Biology of Native Nucleic Acid Modifications [SPP1784]
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5-Formylcytosine (5fC) and 5-formyluracil (5fU) are natural nucleobase modifications that are generated by oxidative modification of 5-methylcytosine and thymine (or 5-methyluracil). Herein, we describe chemoselective labeling of 5-formylpyrimidine nucleotides in DNA and RNA by fluorogenic aldol-type condensation reactions with 2,3,3-trimethylindole derivatives. Mild and specific reaction conditions were developed for 5fU and 5fC to produce hemicyanine-like chromophores with distinct photophysical properties. Residue-specific detection was established by fluorescence readout as well as primer-extension assays. The reactions were optimized on DNA oligonucleotides and were equally suitable for the modification of 5fU- and 5fC-modified RNA. This direct labeling approach of 5-formylpyrimidines is expected to help in elucidating the occurrence, enzymatic transformations, and functional roles of these epigenetic/epitranscriptomic nucleobase modifications in DNA and RNA.
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