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Acylazetine as a dienophile in bioorthogonal inverse electron-demand Diels-Alder ligation. 2014
Sander B Engelsma, and
Lianne I Willems, and
Claudia E van Paaschen, and
Sander I van Kasteren, and
Gijsbert A van der Marel, and
Herman S Overkleeft, and
Dmitri V Filippov
Leiden Institute of Chemistry, Leiden University , P.O. Box 9502, 2300 RA Leiden, The Netherlands.
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.
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Gijsbert A van der Marel, and
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Dmitri V Filippov
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Lianne I Willems, and
Claudia E van Paaschen, and
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Gijsbert A van der Marel, and
Herman S Overkleeft, and
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Journal of the American Chemical Society,
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Lianne I Willems, and
Claudia E van Paaschen, and
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Gijsbert A van der Marel, and
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Dmitri V Filippov
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Herman S Overkleeft, and
Dmitri V Filippov
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Claudia E van Paaschen, and
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Gijsbert A van der Marel, and
Herman S Overkleeft, and
Dmitri V Filippov
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