3-Bromotetrazine: labelling of macromolecules via monosubstituted bifunctional s-tetrazines.

Chemical Science
Simon D SchnellKarl Gademann

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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Citations

Mar 12, 2021·Organic Letters·Simon D SchnellKarl Gademann
Mar 17, 2021·ACS Sensors·Guodong HuJianguo Fang
Jul 23, 2021·Organic Letters·Lukas V HoffKarl Gademann
Dec 18, 2020·ACS Medicinal Chemistry Letters·Andrea DorstKarl Gademann
Sep 14, 2021·The Journal of Organic Chemistry·Andrey BubyrevMikhail Krasavin
Dec 4, 2021·Frontiers in Chemistry·Birthe MeinekeSimon J Elsässer

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Methods Mentioned

BETA
column chromatography
X-ray
NMR

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