Sulfonyl azide-mediated norbornene aziridination for orthogonal peptide and protein labeling

被引:10
作者
Gattner, Michael J. [1 ]
Ehrlich, Michael [1 ]
Vrabel, Milan [1 ]
机构
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
关键词
DIELS-ALDER REACTIONS; TRANSFER-RNA SYNTHETASE; FREE CLICK CHEMISTRY; AMINO-ACIDS; GENETIC-CODE; ALKYNE CYCLOADDITION; PHOTOCLICK-CHEMISTRY; MAMMALIAN-CELLS; LIGATION; STRATEGIES;
D O I
10.1039/c4cc04117h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We describe a new bioconjugation reaction based on the aziridination of norbornenes using electron-deficient sulfonyl azides. The reaction enables to attach various useful tags to peptides and proteins under mild conditions.
引用
收藏
页码:12568 / 12571
页数:4
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