DBCO-TFP ester, product number 11815, is the 2,3,5,6-tetrafluorophenyl (TFP) ester of an aza-dibenzocyclooctyne (DBCO) product used for strain-promoted azide-alkyne cycloaddition (SPAAC, also known as “copper free click chemistry”). The TFP ester reacts selectively and efficiently with amines to form amide bonds. TFP esters are preferred over N-hydroxysuccinimide (NHS) esters because they are more stable to hydrolysis and react more efficiently with amines than NHS esters. Quanta BioDesign, Ltd., has demonstrated this through in-house testing. The DBCO moiety reacts selectively with azides via SPAAC to form stable triazole linkages. Insoluble in water, DBCO-TFP ester 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-TFP ester is acid sensitive. It should not be subjected to pH < 5 during reaction or workup.
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-TFP ester in aqueous media or in cells, it should be conjugated to a water-soluble dPEG® product. Quanta BioDesign, Ltd. offers numerous products for this purpose, including amino alcohols and 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.
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.
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 Edition2010, 49(49), 9422–9425.
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