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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

preprint
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.

History

Email Address of Submitting Author

karl.gademann@uzh.ch

Institution

University of Zurich

Country

Switzerland

ORCID For Submitting Author

0000-0003-3053-0689

Declaration of Conflict of Interest

No conflict of interest

Version Notes

Version 1, November 20, 2019

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