Succinimidyl carbonate/NHS functionalized cyclooctene derivative for incorporation of the cyclooctene moiety into amine containing compounds or biomolecules. Cyclooctenes are useful in strain-promoted copper-free click chemistry cycloaddition reactions with 1,2,4,5-tetrazines. This cyclooctene will react with tetrazine functionalized compounds or biomolecules without the need for a catalyst to result in a stable covalent linkage. The 4+2 inverse electron demand Diels-Alder cycloaddition between trans-cyclooctene and tetrazines is the fastest biologically compatible ligation technology reported and has had many applications in biological labeling and imaging.(E)-Cyclooct-4-enyl 2,5-dioxo-1-pyrrolidinyl carbonate may be used in the synthesis of vancomycin-TCO that can bind to the cell wall of gram-positive bacteria, which can subsequently react with tetrazine (Tz) decorated magneto-fluorescent nanoparticles orthogonally. This bioorthogonal labeling method is useful for the detection of gram-positive bacteria.
1.Melissa L Blackman,Maksim Royzen,Joseph M Fox. (2008-09-19) Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity.. Journal of the American Chemical Society, 130 ((41)):(13518-13519). [PMID:18798613]
2.Neal K Devaraj,Ralph Weissleder,Scott A Hilderbrand. (2008-12-05) Tetrazine-based cycloadditions: application to pretargeted live cell imaging.. Bioconjugate chemistry, 19 ((12)):(2297-2299). [PMID:19053305]
3.Mark R Karver, Ralph Weissleder, Scott A Hilderbrand,. (2011-09-29) Synthesis and evaluation of a series of 1,2,4,5-tetrazines for bioorthogonal conjugation.. Bioconjugate chemistry, 22 ((11)):( 2263-2270 ). [PMID:21950520]
4.Katherine S Yang,Ghyslain Budin,Thomas Reiner,Claudio Vinegoni,Ralph Weissleder. (2012-05-31) Bioorthogonal imaging of aurora kinase A in live cells.. Angewandte Chemie (International ed. in English), 51 ((27)):(6598-6603). [PMID:22644700]
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