DBCO-dPEG®4-TFP ester, product number 11362, is a heterobifunctional, bioorthogonal crosslinker. The tetrafluorophenyl (TFP) ester reacts specifically with free amines to form amide bonds. The dibenzylcyclooctyne (DBCO) moiety reacts selectively with azides via strain-promoted azide-alkyne cycloaddition (SPAAC) to form triazole linkages. An amphiphilic, flexible, single molecular weight, discrete polyethylene glycol (dPEG®) spacer separates the two functional groups. The dPEG® spacer improves the water solubility of the conjugates.
Why use Copper-Free Click Chemistry?
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. Because copper is not part of the reaction, SPAAC reagents can label living cells. (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)
What Makes dPEG® Products Different?
Quanta BioDesign’s dPEG® reagents are superior to traditional, polymeric polyethylene glycol (PEG) reagents. Traditional PEG reagents are dispersed polymers (Đ > 1). Disperse PEG contains a complex mixture of different chain lengths and molecular weights in a Poisson distribution. (3, 4) In contrast, each dPEG® reagent from Quanta BioDesign, Ltd contains a single PEG compound. (4) DBCO-dPEG®4-TFP ester simplifies the analysis of conjugates formed in the crosslinking reactions because the dPEG® crosslinker is a discrete chain length product with a single molecular weight.
TFP esters offer many advantages over traditional N-hydroxysuccinimide (NHS) esters. TFP esters are more stable to hydrolysis in aqueous media compared to NHS esters, even at higher pH ranges. Moreover, Quanta BioDesign has shown through in-house testing that at optimum pH, TFP esters label primary amines more readily than NHS esters.
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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.
Flory, P. J. Molecular Size Distribution in Ethylene Oxide Polymers. J. Am. Chem. Soc.1940, 62(6), 1561–1565.
Davis, P. D.; Crapps, E. C. (Quanta BioDesign, Ltd.). Selective and Specific Preparation of Discrete PEG Compounds. U.S. Patent 7,888,536, February 15, 2011.
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