Strain-Promoted Oxidation-Controlled Cyclooctyne-1,2-Quinone Cycloaddition (SPOCQ) for Fast and Activatable Protein Conjugation

被引：70

作者：

Borrmann, Annika ^{[1
]}

Fatunsin, Olumide ^{[1
]}

Dommerholt, Jan ^{[1
]}

Jonker, Anika M. ^{[1
]}

Lowik, Dennis W. P. M. ^{[1
]}

van Hest, Jan C. M. ^{[1
]}

van Delft, Floris L. ^{[1
]}

机构：

[1] Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 AJ Nijmegen, Netherlands

来源：

BIOCONJUGATE CHEMISTRY | 2015年 / 26卷 / 02期

关键词：

AZIDE-ALKYNE CYCLOADDITION; LIVE MAMMALIAN-CELLS; PHOTOCLICK-CHEMISTRY; AMINO-ACID; BIOORTHOGONAL CHEMISTRY; CHEMICAL-MODIFICATION; RECOMBINANT PROTEINS; LIGATION; CYCLOOCTYNES; DESIGN;

D O I：

10.1021/bc500534d

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页码：257 / 261

页数：5

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