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DBCO-Acid

Dibenzylcyclooctyne-Acid

Product Cat. No. Amount Price (EUR) Buy / Note
DBCO-Acid CLK-A101N-25 25 mg 153,55 Add to Basket/Quote Add to Notepad
DBCO-Acid CLK-A101N-100 100 mg 396,00 Add to Basket/Quote Add to Notepad
DBCO-Acid CLK-A101N-1000 1 g 2.416,44 Add to Basket/Quote Add to Notepad

For research use only!

Shipping: shipped at ambient temperature

Storage Conditions: store at -20 °C

Shelf Life: 12 months

Molecular Formula: C21H19NO3

Molecular Weight: 333.38 g/mol

CAS#: 1425485-72-8

Purity: > 90 % (HPLC, H NMR)

Form: off-white to grey solid

Solubility: DCM, DMF, DMSO, THF

Description:
Simple amine reactive reagent for the introduction of a dibenzylcyclooctyne to an available amine functionality. It can be activated in situ using standard activation methods, e.g., with EDC and NHS in methylene chloride. Once the molecule, e.g. a protein, is DBCO-labeled, it can react with an azide-labeled molecule to produce a stable conjugate (triazole) via Cu(I)-free or strain-promoted click reaction. Because DBCOs and azides are absent from biological systems, there is minimal background labeling of cells or lysates.

Applications:
Protein-peptide conjugates
Peptide-small molecule conjugates
18F radiolabelling
Protein-oligonucleotide conjugates
Surface modification

Important Product Information

Do not use DTT, TCEP or β-mercaptoethanol, because they will reduce the azide.

Copper-free Click Reaction

  • Prepare the azide-containing sample in reaction buffer.
  • Add DBCO-protein conjugate to azide-containing sample.
  • Recommendation: Add 1 mol equivalent of limiting protein to 1.5 - 3.0 mol equivalents of highest abundance protein.
  • Incubate the reaction at room temperature for 2 - 4 hours or at 4 °C for 2 - 12 hours.
  • The reaction is now ready for purification.

Troubleshooting

Problem: Low conjugation of DBCO and azide

  • Possible reason: Suboptimal reaction conditions
    - Increase incubation time
    - Optimize conjugation conditions by altering molar excess
    - Perform conjugation reactions at 37 °C

Selected References:
Simon et al. (2012) Facile Double-Functionalization of Designed Ankyrin Repeat Proteins using Click and Thiol Chemistries. Bioconjugate Chem. 23 (2):279.
Zeng et al. (2012). 64Cu Core-Labeled Nanoparticles with High Specific Activity via Metal-Free Click Chemistry. ACS Nano. 6 (6):5209.
Arumugam et al. (2011). [18F]Azadibenzocyclooctyne ([18F]ADIBO): A biocompatible radioactive labeling synthon for peptides using catalyst free [3+2] cycloaddition. Bioorg. Med. Chem. Lett. 21:6987.
Campbell-Verduyn et al. (2011). Strain-Promoted Copper-Free Click Chemistry for 18F Radiolabeling of Bombesin. Angew. Chem. Int. Ed. 50:11117.
Debets et al. (2010) Aza-dibenzocyclooctynes for fast and efficient enzyme PEGylation via copper-free (3+2) cycloaddition. Chem. Commun. 46:97.