Acylazetine as a Dienophile in Bioorthogonal Inverse Electron-Demand Diels鈥揂lder Ligation

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• 作者：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
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：May 16, 2014
• 年：2014
• 卷：16
• 期：10
• 页码：2744-2747
• 全文大小：255K
• 年卷期：v.16,no.10(May 16, 2014)
• ISSN：1523-7052

文摘

A new bioorthogonal N-acylazetine tag, suitable for tetrazine mediated inverse electron-demand Diels鈥揂lder 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.