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6-Methyl-Tetrazine-PEG5-Alkyne

Cat. No. Amount Price (EUR) Buy / Note
CLK-1013-10 10 mg 137,81 Add to Basket/Quote Add to Notepad
CLK-1013-100 100 mg 912,98 Add to Basket/Quote Add to Notepad
Structural formula of 6-Methyl-Tetrazine-PEG5-Alkyne
Structural formula of 6-Methyl-Tetrazine-PEG5-Alkyne

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: C20H26N4O5

Molecular Weight: 402.44 g/mol

Purity: > 95 % (HPLC)

Form: solid

Solubility: Chloroform, DCM, DMF, DMSO, MeOH

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.

Important Product Information

  • If possible, avoid reducing agents in reaction buffers, this can interfere with the alkyne stability.

Procedure for Azide-Alkyne Click Reaction

  • In order to perform the Cu(I)-catalyzed azide-alkyne click reaction (CuAAC) at least one additional component is required - copper(I) catalyst. However, the general thermodynamic instability of Cu(I), which results in its easy oxidation to inactive Cu (II) usually requires the copper catalyst to be prepared with an appropriate chelating ligand.
  • The selection of partial protocol for CuAAC reaction depends mainly on two factors, including nature of alkyne-modified biopolymer (e.g. cell lysis, fixed cells), and availability of chelating ligand.

Procedure for Tetrazine - TCO Reaction

  • Prepare tetrazine-labeled sample in reaction buffer.
  • Add TCO-labeled sample to tetrazine-labeled sample.
  • Allow reaction to proceed for 30 - 60 minutes at room temperature.
  • Store conjugate at 4°C until ready for purification or use.

Selected References:
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.