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A Benzophenone‐Based Photocaging Strategy for the N7 Position of Guanosine
Author(s) -
Anhäuser Lea,
Klöcker Nils,
Muttach Fabian,
Mäsing Florian,
Špaček Petr,
Studer Armido,
Rentmeister Andrea
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201914573
Subject(s) - nucleobase , chemistry , guanosine , nucleic acid , moiety , stereochemistry , benzophenone , rna , nucleotide , translation (biology) , dna , combinatorial chemistry , biochemistry , organic chemistry , messenger rna , gene
Abstract 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 α‐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.