Acylazetine as a dienophile in bioorthogonal inverse electron-demand Diels-Alder ligation

Sander B. Engelsma, Lianne I. Willems, Claudia E. Van Paaschen, Sander I. Van Kasteren, Gijsbert A. Van Der Marel, Herman S. Overkleeft*, Dmitri V. Filippov

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


A new bioorthogonal N-acylazetine tag, suitable for tetrazine mediated inverse electron-demand Diels-Alder conjugation, is developed. The tag is small and achiral. We demonstrate the usefulness of N-acylazetine-tetrazine based bioorthogonal chemistry in two-step activity-based protein profiling. The performance of the new tetrazinophile in the labeling of catalytically active proteasome subunits was comparable to that of the more sterically demanding norbornene tag.

Original languageEnglish
Pages (from-to)2744-2747
Number of pages4
JournalOrganic Letters
Issue number10
Publication statusPublished - 5 May 2014

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