Strain-promoted oxidation-controlled cyclooctyne-1,2-quinone cycloaddition (SPOCQ) for fast and activatable protein conjugation

A. Borrmann, O. Fatunsin, J. Dommerholt, A.M. Jonker, D.W.P.M. Löwik, J.C.M. van Hest, F.L. van Delft

Research output: Contribution to journalArticleAcademicpeer-review

42 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)257-261
Number of pages5
JournalBioconjugate Chemistry
Volume26
Issue number2
DOIs
Publication statusPublished - 18 Feb 2015
Externally publishedYes

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