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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. 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.

SUBMITTER: Schnell SD 

PROVIDER: S-EPMC8157750 | biostudies-literature |

REPOSITORIES: biostudies-literature

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