DBCO-amine, product number 11750, is an aza-dibenzocyclooctyne (DBCO) product used for strain-promoted azide-alkyne cycloaddition (SPAAC, also known as “copper free click chemistry”). The DBCO moiety reacts selectively with azides via SPAAC to form stable triazole linkages. The amine terminus of the molecule reacts with carboxylic acids and the active esters of carboxylic acids to form amide bonds. Insoluble in water, DBCO-amine is slightly soluble to sparingly soluble in most organic solvents. Quanta BioDesign, Ltd. recommends dimethylsulfoxide (DMSO), N,N’-dimethylformamide (DMF), or N,N’-dimethylacetamide (DMAC) as solvents for this product. DBCO-amine is relatively insensitive to bases and can be used in the presence of aqueous bases. This product is acid sensitive. It should not be subjected to pH < 5 during reaction or workup. The product should always be stored at -20°C when not in use.

The published discovery in 2004 of SPAAC, also known as “copper free click chemistry,” by Carolyn Bertozzi and coworkers improved the click chemistry toolbox. Toxic copper catalysts were eliminated, making the reaction truly bioorthogonal. By removing the copper(I) catalyst from the reaction, living cells can be labeled with reagents designed for SPAAC. (1) Since the original publication, multiple improvements in strained cyclooctyne reagents resulted in the development of DBCO as a nearly perfect azide partner for SPAAC. (2)

To use DBCO-amine in aqueous media or in cells, it must be conjugated to a water-soluble dPEG® product. Quanta BioDesign, Ltd. offers numerous products for this purpose, including hydroxy acids (and their active esters), and protected amino acids. We also offer many DBCO-based dPEG® products already prepared for use.

If you need bulk product in a larger package size than our standard sizes, please contact us for a quote. Our commercial capabilities permit us to manufacture this product at any scale that you need.

Application References:

  1. Agard, N. J.; Prescher, J. A.; Bertozzi, C. R. A Strain-Promoted [3 + 2] Azide−Alkyne Cycloaddition for Covalent Modification of Biomolecules in Living Systems. J. Am. Chem. Soc. 2004, 126(46), 15046–15047.
  2. Dommerholt, J.; Schmidt, S.; Temming, R.; Hendriks, L. J. A.; Rutjes, F. P. J. T.; vanHest, J. C. M.; Lefeber, D. J.; Friedl, P.; van Delft, F. L. Readily Accessible Bicyclononynes for Bioorthogonal Labeling and Three-Dimensional Imaging of Living Cells. Angewandte Chemie International Edition 2010, 49(49), 9422–9425.

Additional information

Weight.5 oz
Dimensions.75 × .75 × 2 in

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