Published TCIMAIL newest issue No.196
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TCO (trans-cyclooctene) Reagents for Bioconjugate Reactions
TCO (trans-cyclooctene) is known as a compound that undergoes a Strain-Promoted Inverse Electron-demand Diels-Alder Cycloaddition (SPIEDAC) with tetrazines. This reaction is widely used in protein labeling and imaging as a bioconjugation reaction.1-4) 4-TCO-NPC equatorial isomer, 4-TCO-NPC axial isomer, 2-TCO-NPC axial isomer, and 2-TCO-NPC equatorial isomer are regio- and stereoisomers of each other and have distinct reactivity. With tetrazines, the reaction rates are 4-TCO > 2-TCO and axial > equatorial. On the other hand, particularly in vivo, where thiol groups are present, the stability is considered to 2-TCO > 4-TCO.5) These reagents easily react with primary amines at the carbonate ester group to give the corresponding carbamates. Furthermore, when it reacts with a tetrazine that has a fluorescent functional group, SPIEDAC gives fluorescence to the carbamate.
Related Products
- T4212
- 4-TCO-NPC equatorial isomer
- T4213
- 4-TCO-NPC axial isomer
- T4218
- 2-TCO-NPC axial isomer
- T4219
- 2-TCO-NPC equatorial isomer
- T3948
- TCO-PEG3-Maleimide
- T3949
- TCO-PEG4-NHS
- T4126
- N-(4E)-TCO-L-lysine
References
- 1) Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels−Alder Reactivity
- 2) Fast and Sensitive Pretargeted Labeling of Cancer Cells through a Tetrazine/trans-Cyclooctene Cycloaddition
- 3) Bioorthogonal Turn-On Probes for Imaging Small Molecules inside Living Cells
- 4) Inverse electron demand Diels–Alder reactions in chemical biology
- 5) Minimal Tags for Rapid Dual-Color Live-Cell Labeling and Super-Resolution Microscopy
