Progress in the Bioorthogonal Labeling Reactions

doi:10.6023/A15030214

Abstract

Selective labeling of biomolecules inside living cells is a challenging task, which requires the reaction to proceed efficiently and selectively under physiological condition without interfering with active species presented in the living systems. Bioorthogonal reactions, which were developed in the past decade, successfully meet these requirements and their applications in biomolecule labeling have expanded our understanding of cellular process. Considerable attention has been focused on the optimization of a few known bioorthogonal reactions, including discovery of new ligands and privileged substrates for transition metal catalyzed reactions, and the use of strain promoted functional group for substrate activation in the cycloaddition reactions. In addition, new bioorthogonal reactions, including the fluorogenic reactions, have also been emerged in the past few years. Progress has also been made toward the development of mutually exclusive bioorthogonal reactions and their application for multiple labeling of biomolecules inside living cells. Here we review the most widely used bioorthogonal labeling reactions, drawing particular attention to those that have been used in living systems. We focused on the selective labeling of target proteins by means of site-specific introduction of a functional group followed by the bioorthogonal reaction with a complementary functional group. We categorized these reactions into three different groups based on the catalysts used in the reactions: metal catalyzed reactions, photo induced reactions and reactions without catalyst. The biological applications of these bioorthogonal reactions have also been briefly introduced. We also listed the rate constants and main references of these reactions to facilitate researchers for choosing the appropriate one. Lastly, we highlight ongoing challenges in developing new bioorthogonal reactions and their application to study complex biological systems.

Key words: bioorthogonal reaction, living cells, protein labeling, site-specific, unnatural amino acid

Cite this article

Yang Maiyun, Chen Peng R.. Progress in the Bioorthogonal Labeling Reactions[J]. Acta Chim. Sinica, 2015, 73(8): 783-792.

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