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Updated: Nov 2, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
3-Bromotetrazine: labelling of macromolecules via monosubstituted bifunctional s-tetrazines
Simon D Schnell1, Lukas V Hoff1, Advaita Panchagnula1
1University of Zurich Winterthurerstrasse 190 8057 Zurich Switzerland Karl.Gademann@uzh.ch.
Abstract:
We report the synthesis and first characterisation of the novel chemical probe 3-bromotetrazine and establish its reactivity towards nucleophiles. This led to the synthesis of several novel classes of 3-monosubstituted s-tetrazines. A remarkable functional group selectivity is observed and is utilised to site-selectively functionalise different complex molecules. The stability of 3-bromotetrazine under the reaction conditions facilitated the development of a protocol for protein functionalisation, which enabled a "minimal", bifunctional tetrazine unit as a bio-orthogonal handle for inverse electron demand Diels-Alder reactions. Additionally, 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.
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