Topics in Current Chemistry

, 374:1 | Cite as

Photo-Triggered Click Chemistry for Biological Applications

Review
Part of the following topical collections:
  1. Cycloadditions in Bioorthogonal Chemistry

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.

Keywords

Bioorthogonal reaction Photo-triggered reaction Photoclick Tetrazole Nitrile imine Azirine Cyclopropenone o-Naphthoquinone methide o-Quinodimethanes Hetero Diels–Alder reaction 

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

Notes

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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Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  1. 1.Department of ChemistryState University of New York at BuffaloBuffaloUSA

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