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  Fluorogenic labeling of 5-formylpyrimidine nucleotides in DNA and RNA.

Samanta, B., Seikowski, J., & Höbartner, C. (2016). Fluorogenic labeling of 5-formylpyrimidine nucleotides in DNA and RNA. Angewandte Chemie International Edition, 55(5), 1912-1916. doi:10.1002/anie.201508893.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0029-C38E-1 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-002D-1941-E
Genre: Journal Article

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Samanta, B.1, Author              
Seikowski, J.1, Author              
Höbartner, C.1, Author              
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1Research Group of Nucleic Acid Chemistry, MPI for Biophysical Chemistry, Max Planck Society, ou_578605              

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Free keywords: DNA; Epigenetics; Fluorogenic probes; Modified nucleobases; RNA
 Abstract: 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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Language(s): eng - English
 Dates: 2015-12-172016-01-26
 Publication Status: Published in print
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 Rev. Method: Peer
 Identifiers: DOI: 10.1002/anie.201508893
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Title: Angewandte Chemie International Edition
Source Genre: Journal
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Pages: - Volume / Issue: 55 (5) Sequence Number: - Start / End Page: 1912 - 1916 Identifier: -