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3-Bromotetrazine: Labelling of Macromolecules via Monosubstituted Bifunctional s-Tetrazines

Abstract

We report the synthesis and first characterisation of the novel chemical probe 3-bromotetrazine and establish its reactivity towards nucleophiles leading 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 installing 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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Article information


Submitted
05 Dec 2019
Accepted
09 Feb 2020
First published
10 Feb 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Accepted Manuscript
Article type
Edge Article

3-Bromotetrazine: Labelling of Macromolecules via Monosubstituted Bifunctional s-Tetrazines

S. D. Schnell, L. V. Hoff, A. Panchagnula, M. H. H. Wurzenberger, T. M. Klapoetke, S. Sieber, A. Linden and K. Gademann, Chem. Sci., 2020, Accepted Manuscript , DOI: 10.1039/C9SC06169J

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