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

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

Journal of the American Chemical Society (2008-09-19)
Melissa L Blackman, Maksim Royzen, Joseph M Fox
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
TCO-amine HCl salt
Sigma-Aldrich
(E)-Cyclooct-4-enol
Sigma-Aldrich
Cyclooctane, ≥99%
Sigma-Aldrich
TCO PEG4 succinimidyl ester
Sigma-Aldrich
(E)-Cyclooct-4-enyl 2,5-dioxo-1-pyrrolidinyl carbonate
Sigma-Aldrich
(4-(1,2,4,5-Tetrazin-3-yl)phenyl)methanamine hydrochloride, 95%