1055982-99-4Relevant academic research and scientific papers
Tetrazine ligation: Fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity
Blackman, Melissa L.,Royzen, Maksim,Fox, Joseph M.
, p. 13518 - 13519 (2008)
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. Copyright
TETRAZINE-BASED BIO-ORTHOGONAL COUPLING REAGENTS AND METHODS
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Page/Page column 11; 16, (2009/02/11)
Coupling reactions, suitable for use in organic or aqueous media, are performed by contacting a 1,2,4,5-tetrazine with a dienophile. The dienophile may be covalently bonded to a protein, and the coupling reaction may be performed in biological media such as those containing cells or cell lysates. The reactions may be performed in the presence of primary amines, thiols, acetylenes, azides, phosphines, and products of Staudinger and/or Sharpless-Huisgen reactions Novel 3-substituted cyclopropene compounds and trans-cyclooctenes are exemplary dienophiles for these reactions.
