title: Strain-promoted oxidation-controlled cyclooctyne-1,2-quinone cycloaddition (SPOCQ) for fast and activatable protein conjugation.
abstract: A main challenge in the area of bioconjugation is to devise reactions that are both activatable and fast. Here, we introduce a temporally controlled reaction between cyclooctynes and 1,2-quinones, induced by facile oxidation of 1,2-catechols. This so-called strain-promoted oxidation-controlled cyclooctyne-1,2-quinone cycloaddition (SPOCQ) shows a remarkably high reaction rate when performed with bicyclononyne (BCN), outcompeting the well-known cycloaddition of azides and BCN by 3 orders of magnitude, thereby allowing a new level of orthogonality in protein conjugation.
authors.affiliation: Bioorganic Chemistry and Synthetic Organic Chemistry, Institute for Molecules and Materials, Radboud University Nijmegen , 6525 AJ Nijmegen, The Netherlands.
authors.forename: Annika
authors.initials: A
authors.lastname: Borrmann
authors.forename: Olumide
authors.initials: O
authors.lastname: Fatunsin
authors.forename: Jan
authors.initials: J
authors.lastname: Dommerholt
authors.forename: Anika M
authors.initials: AM
authors.lastname: Jonker
authors.forename: Dennis W P M
authors.initials: DW
authors.lastname: Löwik
authors.forename: Jan C M
authors.initials: JC
authors.lastname: van Hest
authors.forename: Floris L
authors.initials: FL
authors.lastname: van Delft
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D002396:Catechols / Q000737:chemistry*; D057930:Click Chemistry; D003500:Cyclization; D061565:Cycloaddition Reaction; D008958:Models, Molecular; D011506:Proteins / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001386:Azides; D002396:Catechols; D011506:Proteins; D011809:Quinones; C042001:1-octyne