title: Acylazetine as a dienophile in bioorthogonal inverse electron-demand Diels-Alder ligation.
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.
authors.affiliation: Leiden Institute of Chemistry, Leiden University , P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Sander B
authors.initials: SB
authors.lastname: Engelsma
authors.forename: Lianne I
authors.initials: LI
authors.lastname: Willems
authors.forename: Claudia E
authors.initials: CE
authors.lastname: van Paaschen
authors.forename: Sander I
authors.initials: SI
authors.lastname: van Kasteren
authors.forename: Gijsbert A
authors.initials: GA
authors.lastname: van der Marel
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
authors.forename: Dmitri V
authors.initials: DV
authors.lastname: Filippov
mesh_terms: D001384:Azetidines / Q000737:chemistry*; D004583:Electrons; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry*; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D001384:Azetidines; D006573:Heterocyclic Compounds, 1-Ring; D006574:Heterocyclic Compounds, 2-Ring