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Acylazetine as a Dienophile in Bioorthogonal Inverse Electron-Demand Diels–Alder Ligation

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journal contribution
posted on 16.05.2014, 00:00 by 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
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.