Extending the Palette of Green Coumarin Photocages – Oligonucleotide Fragmentation and Superior 5’‐Caps

Abstract

AbstractThe possibilities of dicyanocoumarin (DCCM)‐modified oligonucleotides are expanded 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). Furthermore, an answer to the decreasing uncaging quantum yields often faced when working with red‐shifted photocages is given 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 more bioconjugation reactions. Due to their planarization, they even experience an additional red‐shift which is important for their use in biological applications.