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
  • M. L. Blackman, M. Royzen, J. M. Fox, J. Am. Chem. Soc. 2008, 130, 13518.
• 2) Fast and Sensitive Pretargeted Labeling of Cancer Cells through a Tetrazine/trans-Cyclooctene Cycloaddition
  • N. K. Devaraj, R. Upadhyay, J. B. Haun, S. A. Hilderbrand, R. Weissleder, Angew. Chem. Int. Ed. 2009, 48, 7013.
• 3) Bioorthogonal Turn-On Probes for Imaging Small Molecules inside Living Cells
  • N. K. Devaraj, S. Hilderbrand, R. Upadhyay, R. Mazitschek, R. Weissleder, Angew. Chem. Int. Ed. 2010, 49, 2869.
• 4) Inverse electron demand Diels–Alder reactions in chemical biology
  • B. L. Oliveira, Z. Guo, G. J. L. Bernardes, Chem. Soc. Rev. 2017, 46, 4895.
• 5) Minimal Tags for Rapid Dual-Color Live-Cell Labeling and Super-Resolution Microscopy
  • I. Nikić, T. Plass, O. Schraidt, J. Szymański, J. A. G. Briggs, C. Schultz, E. A. Lemke, Angew. Chem. Int. Ed. 2014, 53, 2245.

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