ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
Schnell_et_al.pdf (3.78 MB)
0/0

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

preprint
submitted on 20.11.2019 and posted on 28.11.2019 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

Exports