Title
Extending the Palette of Green Coumarin Photocages – Oligonucleotide Fragmentation and Superior 5’-Caps
Author
Kaufmann, Janik, Jonas Wolf, and Alexander Heckel
Year
2023
Journal
Chemistry – A European Journal
Abstract
We extend the possibilities of dicyanocoumarin (DCCM)-modified oligonucleotides to not just allow their release and therefore activation with green light (OFF ? ON) but to also now offer a solution for their fragmentation after exposure to green light (ON ? OFF). We further give an answer to the decreasing uncaging quantum yields often faced when working with red-shifted photocages and showed that rigidified DCCM 5?-caps outperform their predecessors. Those two new 5?-caps with ATTO 390 motif or julolidine core are compatible with copper(I)-catalyzed alkyne-azide cycloadditions (CuAACs) and therefore suitable for efficient caging through cyclization or for more bioconjugation reactions. Due to their planarization, they even experience an additional red-shift which is important for their use in biological applications.
Instrument
V-650
Keywords
photochemistry,oligonucleotides,click chemistry,photolabile protecting group