Inverse Electron-Demand Diels–Alder Bioorthogonal Reactions

Topics in Current Chemistry volume 374, Article number: 3 (2016) Cite this article

Abstract

Bioorthogonal reactions have been widely used over the last 10 years for imaging, detection, diagnostics, drug delivery, and biomaterials. Tetrazine reactions are a recently developed class of inverse electron-demand Diels–Alder reactions used in bioorthogonal applications. Given their rapid tunable reaction rate and highly fluorogenic properties, tetrazine bioorthogonal reactions have come to be considered highly attractive tools for elucidating biological functions and messages in vitro and in vivo. In this chapter, we present recent advances expanding the scope of precursor reactivity and we introduce new biomedical methodology based on bioorthogonal tetrazine chemistry. We specifically highlight novel applications for different kinds of biomolecules, including nucleic acid, protein, antibodies, lipids, glycans, and bioactive small molecules, in the areas of imaging, detection, and diagnostics. We also briefly present other recently developed inverse electron-demand Diels–Alder bioorthogonal reactions. Lastly, we consider future directions and potential roles that inverse electron-demand Diels–Alder reactions may play in the fields of bioorthogonal and biomedical chemistry.

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Acknowledgments

The authors gratefully acknowledge S. Alexander and C.Y. Zhou for their many helpful discussions and suggestions. We thank the University of California, San Diego, for financial support.

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  1. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, Urey Hall 4120, La Jolla, CA, 92093, USA

    Haoxing Wu & Neal K. Devaraj

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  1. Haoxing Wu
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  2. Neal K. Devaraj
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Correspondence to Neal K. Devaraj.

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Wu, H., Devaraj, N.K. Inverse Electron-Demand Diels–Alder Bioorthogonal Reactions. Top Curr Chem (Z) 374, 3 (2016). https://doi.org/10.1007/s41061-015-0005-z

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Keywords

  • Diels–Alder
  • Tetrazine
  • Bioorthogonal
  • Imaging
  • Detection