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Chemo-enzymatic strategies provide a highly selective means to label different classes of biomolecules in vitro , but also in vivo . In the field of RNA, efficient labeling of eukaryotic mRNA with small organic reporter molecules would provide a way to detect endogenous mRNA and is therefore highly attractive. Although more and more bioorthogonal reactions are being reported, they can only be applied to chemo-enzymatic strategies if a suitable ( i.e. , click compatible) modification can be introduced into the RNA of interest. We report enzymatic site-specific transfer of a 4-vinylbenzyl group to the 5'-cap typical of eukaryotic mRNAs. The 4-vinylbenzyl group gives access to mRNA labeling using the inverse electron-demand Diels-Alder reaction, which does not work with an enzymatically transferred allyl group. The 4-vinylbenzyl-modified 5'-cap can also be converted in a photoclick reaction generating a "turn-on" fluorophore. Both click reactions are bioorthogonal and the two step approach also works in eukaryotic cell lysate. Enzymatic transfer of the 4-vinylbenzyl group addresses the lack of flexibility often attributed to biotransformations and thus advances the potential of chemo-enzymatic approaches for labeling.

Enzymatic modification of 5′-capped RNA with a 4-vinylbenzyl group provides a platform for photoclick and inverse electron-demand Diels–Alder reaction