A photoinducible 1,3-dipolar cycloaddition reaction for rapid, selective modification of tetrazole-containing proteins

被引:334
作者
Song, Wenjiao [1 ]
Wang, Yizhong [1 ]
Qu, Jun [2 ]
Madden, Michael M. [1 ]
Lin, Qing [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
[2] SUNY Buffalo, Dept Pharmaceut Sci, Buffalo, NY 14260 USA
关键词
alkenes; biotechnology; dipolar cycloaddition; photolysis; proteins;
D O I
10.1002/anie.200705805
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) Reactive but biologically inert: The bioorthogonal title reaction enables highly specific chemical modifications, such as lipidation, of engineered proteins containing a diphenyltetrazole group (see scheme). The cycloaddition in biological media is extremely fast (≤1 min) and tolerant of proteinaceous groups. Strongly fluorescent pyrazoline cycloadducts are generated with simple alkenes. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2832 / 2835
页数:4
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