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J Am Chem Soc. 2008 Oct 15;130(41):13518-9. doi: 10.1021/ja8053805. Epub 2008 Sep 18.

Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity.

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  • 1Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA.


Described is a bioorthogonal reaction that proceeds with unusually fast reaction rates without need for catalysis: the cycloaddition of s-tetrazine and trans-cyclooctene derivatives. The reactions tolerate a broad range of functionality and proceed in high yield in organic solvents, water, cell media, or cell lysate. The rate of the ligation between trans-cyclooctene and 3,6-di-(2-pyridyl)-s-tetrazine is very rapid (k2 2000 M-1 s-1). This fast reactivity enables protein modification at low concentration.

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