Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 8, Pages 3161-3165Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201914573
Keywords
benzophenone; N7G; photocaging; RNA; RNA modification
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Funding
- Deutsche Forschungsgemeinschaft [RE2796/6-1]
- European Research Council [77280]
- Fonds der Chemischen Industrie
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Selective modification of nucleobases with photolabile caging groups enables the study and control of processes and interactions of nucleic acids. Numerous positions on nucleobases have been targeted, but all involve formal substitution of a hydrogen atom with a photocaging group. Nature, however, also uses ring-nitrogen methylation, such as m(7)G and m(1)A, to change the electronic structure and properties of RNA and control biomolecular interactions essential for translation and turnover. We report that aryl ketones such as benzophenone and alpha-hydroxyalkyl ketone are photolabile caging groups if installed at the N7 position of guanosine or the N1 position of adenosine. Common photocaging groups derived from the ortho-nitrobenzyl moiety were not suitable. Both chemical and enzymatic methods for site-specific modification of N7G in nucleosides, dinucleotides, and RNA were developed, thereby opening the door to studying the molecular interactions of m(7)G and m(1)A with spatiotemporal control.
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