Strain-Promoted Oxidation-Controlled Cyclooctyne鈥?,2-Quinone Cycloaddition (SPOCQ) for Fast and Activatable Protein Conjugation

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• 作者：Annika Borrmann ; Olumide Fatunsin ; Jan Dommerholt ; Anika M. Jonker ; Dennis W. P. M. L枚wik ; Jan C. M. van Hest ; Floris L. van Delft
• 刊名：Bioconjugate Chemistry
• 出版年：2015
• 出版时间：February 18, 2015
• 年：2015
• 卷：26
• 期：2
• 页码：257-261
• 全文大小：276K
• ISSN：1520-4812

文摘

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鈥?,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.