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Schnell_et_al.pdf (3.78 MB)

3-Bromotetrazine: A Versatile Precursor for the Synthesis of 3-Monosubstituted s-Tetrazines and the Labelling of Macromolecules

submitted on 20.11.2019, 11:45 and posted on 28.11.2019, 08:58 by Simon Schnell, Lukas Hoff, Advaita Panchagnula, Simon Sieber, Anthony Linden, Karl Gademann

We report the synthesis of the novel precursor 3-bromotetrazine and its successful use in the synthesis of various families of 3-monosubstituted s-tetrazines. A remarkable functional group selectivity is utilized to site-selectively functionalize different complex molecules. The unexpected stability of 3- bromotetrazine in aqueous media facilitated the development of a protocol for protein functionalization in- stalling a tetrazine unit as a bio-orthogonal handle for inverse electron demand Diels-Alder reactions. Addi- tionally, a novel tetrazine-based chemical probe was developed and its application in the context of thiol- targeted natural product isolation and labelling of mammalian cells is demonstrated.


Email Address of Submitting Author


University of Zurich



ORCID For Submitting Author


Declaration of Conflict of Interest

No conflict of interest

Version Notes

Version 1, November 20, 2019