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These are preliminary reports that have not been peer-reviewed.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.
1/1
0/0

Potassium Arylethynyltrifluoroborate as an Unstrained Dienophile for Ultrafast and On Demand Activation of Bioorthogonal IEDDA Reactions

preprint
submitted on 24.04.2019 and posted on 25.04.2019 by Zijian Guo, Bruno Oliveira, Claudio D. Navo, Pedro M. S. D. Cal, Francisco Corzana, Gonzalo Jiménez-Osés, Gonçalo Bernardes

Strained alkenes and alkynes are the predominant dienophiles used in inverse electron-demand Diels-Alder (IEDDA) reactions, however, their instability, cross-reactivity and accessibility are problematic. Unstrained dienophiles, although physiologically stable and synthetically accessible, react with tetrazines significantly slower relative to strained variants. Here we report the development of potassium arylethynyltrifluoroborates as unstrained dienophiles for ultrafast, chemically triggered IEDDA reactions. By varying the substituents on the tetrazine (e.g. pyridyl- to benzyl-substituents), cycloaddition rates can vary from nearly spontaneous (t1/2≈ 9 s) to no reaction with the unstrained alkyne-BF3 dienophile. The reported system was applied to protein modification and enabled mutually orthogonal labelling of two distinct proteins.

History

Email Address of Submitting Author

gb453@cam.ac.uk

Institution

University of Cambridge

Country

United Kingdom

ORCID For Submitting Author

0000-0001-6594-8917

Declaration of Conflict of Interest

The authors declare no competing financial interests.

Exports

Logo branding

Exports