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

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Published copy (DOI)

Author(s)

  • 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

Department/unit(s)

Publication details

JournalOrganic Letters
DatePublished - 5 May 2014
Issue number10
Volume16
Number of pages4
Pages (from-to)2744-2747
Original languageEnglish

Abstract

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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