用于快速且与活细胞兼容的螯合辅助铜催化叠氮化物-炔烃环加成共轭反应的还原性低聚糖的一步衍生化
One-Step Derivatization of Reducing Oligosaccharides for Rapid and Live-Cell-Compatible Chelation-Assisted CuAAC Conjugation.
作者信息
Machida Takuya, Winssinger Nicolas
机构信息
Department of Organic Chemistry, NCCR Chemical Biology, University of Geneva, 30 quai Ernest Ansermet, 1211, Geneva, Switzerland.
出版信息
Chembiochem. 2016 May 3;17(9):811-5. doi: 10.1002/cbic.201600003. Epub 2016 Mar 31.
We report a new reagent for the functionalization of unprotected oligosaccharides with a picolyl azide group at the anomeric position for chelation-assisted copper-catalyzed alkyne-azide cycloaddition (CuAAC) glycoconjugation. We show that oligosaccharides functionalized with this moiety react with an apparent second-order rate constant of 193 m(-1) s(-1) and can be used to functionalize biomolecules bearing alkyne moieties introduced through metabolic labeling, including in live cells.
我们报道了一种新型试剂，可用于在异头位置用吡啶甲基叠氮基团对未保护的寡糖进行功能化，以实现螯合辅助的铜催化炔烃-叠氮环加成（CuAAC）糖缀合反应。我们表明，用该部分功能化的寡糖以193 m⁻¹ s⁻¹的表观二级速率常数发生反应，并且可用于对通过代谢标记引入炔烃部分的生物分子进行功能化，包括在活细胞中。
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