Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity.
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.
Blackman
Melissa L
ML
Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA.
Royzen
Maksim
M
Fox
Joseph M
JM
D002851:Chromatography, High Pressure Liquid; D034242:Cyclooctanes / Q000138:chemical synthesis / Q000737:chemistry; D004583:Electrons; D015394:Molecular Structure; D021241:Spectrometry, Mass, Electrospray Ionization; D013777:Tetrazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013997:Time Factors
D034242:Cyclooctanes; D013777:Tetrazoles; C474479:cyclooctane
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