1609019-59-1Relevant academic research and scientific papers
Reaction Rates of Various N-Acylenamines in the Inverse-Electron-Demand Diels–Alder Reaction
Engelsma, Sander B.,van den Ende, Thomas C.,Overkleeft, Hermen S.,van der Marel, Gijsbert A.,Filippov, Dmitri V.
, p. 2587 - 2591 (2018/05/03)
In light of the bioorthogonal inverse-electron-demand Diels–Alder strategy, an extended investigation into the effects of ring strain and electron inductive effects on the reactivity of the N-acylenamine core towards tetrazine has been carried out. Through a comparative study between N-acylazetines, N-vinylcarbamates and an N-vinylamide it was shown that ring strain has a more significant effect on reaction rate than electron donation. A significantly improved synthetic route is reported for the preparation of an N-acylazetine biorthogonal tag we have invented previously.
Acylazetine as a dienophile in bioorthogonal inverse electron-demand Diels-Alder ligation
Engelsma, Sander B.,Willems, Lianne I.,Van Paaschen, Claudia E.,Van Kasteren, Sander I.,Van Der Marel, Gijsbert A.,Overkleeft, Herman S.,Filippov, Dmitri V.
supporting information, p. 2744 - 2747 (2014/06/09)
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.
