DBCO-dPEG®24-TFP ester, product number 11370, 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. A flexible, hydrophilic, single molecular weight, discrete polyethylene glycol (dPEG®) spacer separates the two functional groups.
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. SPAAC reagents permit the labeling of live cells due to the removal of copper from the reaction mixture. (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)
TFP Esters vs. NHS Esters
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. Published research by Wang, et al., support this finding. (3)
PEGylation with dPEG® Reagents
Conventional PEG reagents are dispersed polymers (Đ > 1). Dispersed PEG polymers contain a complex mixture of different chain lengths and molecular weights in a Poisson distribution. (4, 5)
Quanta BioDesign’s dPEG® reagents are superior to traditional, polymeric polyethylene glycol (PEG) reagents. In contrast to conventional PEG reagents, each dPEG® reagent from Quanta BioDesign, Ltd contains a single PEG compound. (5) We synthesize and build up our dPEG® reagents from high purity starting materials rather than by polymerization. Thus, our dPEG® products are monodispersed (Ð = 1). The analysis of conjugates that contain dPEG® linkers is simplified because the dPEG® crosslinker is a product with a discrete chain length and a single molecular weight.
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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.; van Hest, 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.
Wang, J.; Zhang, R.-Y.; Wang, Y.-C.; Chen, X.-Z.; Yin, X.-G.; Du, J.-J.; Lei, Z.; Xin, L.-M.; Gao, X.-F.; Liu, Z.; et al. Polyfluorophenyl Ester-Terminated Homobifunctional Cross-Linkers for Protein Conjugation. Synlett2017, 28(15), 1934–1938. https://doi.org/10.1055/s-0036-1590974.
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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