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

doi:10.1021/ol501049c

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	2744-2747
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	10
DOIs	https://doi.org/10.1021/ol501049c
Publication status	Published - 5 May 2014

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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.",

author = "Engelsma, {Sander B.} and Willems, {Lianne I.} and {Van Paaschen}, {Claudia E.} and {Van Kasteren}, {Sander I.} and {Van Der Marel}, {Gijsbert A.} and Overkleeft, {Herman S.} and Filippov, {Dmitri V.}",

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T1 - Acylazetine as a dienophile in bioorthogonal inverse electron-demand Diels-Alder ligation

AU - Engelsma, Sander B.

AU - Willems, Lianne I.

AU - Van Paaschen, Claudia E.

AU - Van Kasteren, Sander I.

AU - Van Der Marel, Gijsbert A.

AU - Overkleeft, Herman S.

AU - Filippov, Dmitri V.

PY - 2014/5/5

Y1 - 2014/5/5

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84900848071&partnerID=8YFLogxK

U2 - 10.1021/ol501049c

DO - 10.1021/ol501049c

M3 - Article

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EP - 2747

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 10

ER -

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

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