全氟芳基叠氮化物 Staudinger 反应：一种快速且生物正交的反应。
Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction.
机构信息
Department of Chemistry, University of Massachusetts Lowell, 1 University Ave., Lowell, MA, 01854, USA.
Department of Chemistry, KTH-, Royal Institute of Technology, Teknikringen 30, 10044, Stockholm, Sweden.
出版信息
Angew Chem Int Ed Engl. 2017 Sep 25;56(40):12117-12121. doi: 10.1002/anie.201705346. Epub 2017 Sep 1.
Abstract
We report a fast Staudinger reaction between perfluoroaryl azides (PFAAs) and aryl phosphines, which occurs readily under ambient conditions. A rate constant as high as 18 m s was obtained between methyl 4-azido-2,3,5,6-tetrafluorobenzoate and methyl 2-(diphenylphosphanyl)benzoate in CD CN/D O. Furthermore, the iminophosphorane product was stable toward hydrolysis and aza-phosphonium ylide reactions. This PFAA Staudinger reaction proved to be an excellent bioothorgonal reaction. PFAA-derivatized mannosamine and galactosamine were successfully transformed into cell-surface glycans and efficiently labeled with phosphine-derivatized fluorophore-conjugated bovine serum albumin.
摘要
我们报告了一种在环境条件下即可快速进行的全氟芳基叠氮化物（PFAAs）与芳基膦之间的Staudinger 反应。在 CD 3 CN/D 2 O 中，甲酯 4-叠氮-2,3,5,6-四氟苯甲酸酯和甲酯 2-(二苯基膦基)苯甲酸酯之间的速率常数高达 18 m s -1 。此外，亚氨基磷叶立德产物对水解和氮杂磷叶立德反应稳定。该 PFAAS Staudinger 反应被证明是一种出色的生物正交反应。PFAAs 衍生的甘露糖胺和半乳糖胺成功转化为细胞表面聚糖，并与膦衍生的荧光团缀合牛血清白蛋白有效标记。
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