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Photo-Triggered Click Chemistry for Biological Applications

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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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Correspondence to Qing Lin.

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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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