Abstract
In the last decade and a half, numerous bioorthogonal reactions have been developed with a goal to study biological processes in their native environment, i.e., in living cells and animals. Among them, the photo-triggered reactions offer several unique advantages including operational simplicity with the use of light rather than toxic metal catalysts and ligands, and exceptional spatiotemporal control through the application of an appropriate light source with pre-selected wavelength, light intensity and exposure time. While the photoinduced reactions have been studied extensively in materials research, e.g., on macromolecular surface, the adaptation of these reactions for chemical biology applications is still in its infancy. In this chapter, we review the recent efforts in the discovery and optimization the photo-triggered bioorthogonal reactions, with a focus on those that have shown broad utility in biological systems. We discuss in each cases the chemical and mechanistic background, the kinetics of the reactions and the biological applicability together with the limiting factors.
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Abbreviations
- 2PE:
-
Two-photon excitation
- CuAAC:
-
Cu-catalyzed azide–alkyne cycloaddition
- DA:
-
Diels–Alder
- ε :
-
Absorption coefficient
- Φ :
-
Quantum yield
- HOMO :
-
Highest occupied molecular orbital
- λ :
-
Wavelength
- LUMO:
-
Lowest unoccupied molecular orbital
- PB:
-
Phosphate buffer
- PBS:
-
Phosphate buffered saline
- PG:
-
Protecting group
- SPAAC:
-
Strain-promoted azide–alkyne cycloaddition
- UAA:
-
Unnatural amino acid
- UV:
-
Ultraviolet
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Acknowledgments
Work on the tetrazole-based photoclick chemistry in QL lab was supported by the National Institutes of Health (GM 085092). AH thanks the Rosztoczy Foundation (to A.H.) for a scholarship.
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Herner, A., Lin, Q. Photo-Triggered Click Chemistry for Biological Applications. Top Curr Chem (Z) 374, 1 (2016). https://doi.org/10.1007/s41061-015-0002-2
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DOI: https://doi.org/10.1007/s41061-015-0002-2