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TCO-Amine

trans-Cyclooctene-Amine

HCl salt

Cat. No. Amount Price (EUR) Buy / Note
CLK-1021-25 25 mg 293,30 Add to Basket/Quote Add to Notepad
CLK-1021-100 100 mg 778,20 Add to Basket/Quote Add to Notepad
CLK-1021-1G 1 g 4.489,30 Add to Basket/Quote Add to Notepad
Structural formula of TCO-Amine (trans-Cyclooctene-Amine, HCl salt)
Structural formula of TCO-Amine

For research use only!

Shipping: shipped at ambient temperature

Storage Conditions: store at -20 °C

Shelf Life: 12 months after date of delivery

Molecular Formula: C12H22N2O2

Molecular Weight: 226.32 g/mol

CAS#: 1609659-02-0

Purity: > 95 % (functionalization with DBCO-NHS ester followed by HPLC)

Form: solid

Solubility: Chloroform, DCM, DMF, DMSO

Applications:
Protein-protein conjugates
Protein-antibody conjugates
Protein-small molecule conjugates
18F radiolabelling
Protein-oligonucleotide conjugates
Surface modification

Description:
The inverse-electron demand Diels-Alder cycloaddition reaction of trans-Cyclooctenes (TCO) with tetrazines is a bioorthogonal reaction that possesses exceptional kinetics (k > 800 M-1s-1) and selectivity. Such excellent reaction rate constants are unparalleled by any other bioorthogonal reaction pair described to date.
The extremely fast kinetics and selectivity enables the conjugation of two low abundance biopolymers in an aqueous and otherwise complex chemical environment through the formation of a stable dihydropyridazine. This bioorthogonal reaction possesses extreme selectivity and biocompatibility, such that the complimentary reagents can form covalent bonds within richly functionalized biological systems, in some cases, living organisms. The TCO-tetrazine click reaction is a very powerful tool in catalyst-free protein-protein bioconjugation.

Advanced Features

  • By far, the fastest kinetics among any other bioorthogonal reaction pairs
  • Reactions complete in 30-60 minutes at low protein concentrations (5-10 μM)
  • TCO functional group remains stable in aqueous buffered media (weeks at 4°C, pH 7.5)
  • Conjugation efficiency > 99 % without requiring a toxic catalyst (e.g. Cu(I))

Important Product Information

  • TCO-Amine is supplied as HCl salt. When using this product, the presence of HCl needs to be compensated with the supplemental addition of 1.1 equivalents of a base. When reacting in an organic solvent we recommend to use triethylamine, diisopropylethylamine or 2,6-lutidine, e.g. when reacting with active esters.

Product Citations:
Please click the black arrow on the right to expand the citation list. Click publication title for the full text.

Selected References:
Karver et al. (2012) Bioorthogonal Reaction Pairs Enable Simultaneous, Selective, Multi-Target Imaging. Angew. Chem. Int. Ed. 51:920.
Devaraj et al. (2009) Fast and Sensitive Pre-Targeted Labeling of Cancer Cells through a Tetrazine/trans-Cyclooctene Cycloaddition. Angew. Chem. Int. Ed. 48:7013.
Haun et al. (2009) Probing Intracellular Biomarkers and Mediators of Cell Activation Using Nanosensor and Bioorthogonal Chemistry. ACS Nano. 5:3204.
Blackman et al. (2008) Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels-Alder Reactivity. J. Am. Chem. Soc. 130:13518.
Devaraj et al. (2008) Tetrazine-Based Cycloadditions: Application to Pretargeted Live Cell Imaging. Bioconjugate Chem. 19:2297.