Photo-Click Labeling and  Ligation

Photo-triggering of the metal-free azide to acetylene cycloaddition reaction was achieved by masking the triple bond of dibenzocyclooctynes as cyclopropenone. Such masked cyclooctynes do not react with azides in the dark. Irradiation of cyclopropenones results in the efficient (t₃₅₅ = 0.33) and clean regeneration of the corresponding dibenzocyclooctynes, which then undergo facile catalyst-free cycloadditions with azides to give corresponding triazoles under ambient conditions. In-situ light activation of a cyclopropenone linked to biotin made it possible to label living cells expressing glycoproteins containing N-azidoacetyl-sialic acid. The cyclopropenone-based “photo-click” chemistry offers exciting opportunities to label living organisms with temporal and spatial resolution and may be used in the preparation of microarrays.

We offer custom synthesis of dibenzocyclooctynes and corresponding cyclopropenones for metal-free click ligation, selective labeling, and surface derivatization.

Labeling of live cells is conducted in collaboration with Professor Boons group:

Patterned Surface Photo-Derivatization