DBCO-dPEG®12-TFP ester, product number 11366, 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, single molecular weight, discrete polyethylene glycol (dPEG®) spacer separates the functional groups at each end of the molecule. This dPEG® spacer increases the molecule’s hydrophilicity.
Click Chemistry and PEGylation
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 of the removal of copper from 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)
Quanta BioDesign’s dPEG® reagents are superior to traditional, polymeric polyethylene glycol (PEG) reagents. Because they form from polymeric processes, conventional PEG reagents are dispersed polymers (Đ > 1). Disperse PEG contains a complex mixture of different chain lengths and molecular weights in a Poisson distribution. (4, 5) In contrast, each dPEG® reagent from Quanta BioDesign, Ltd contains a single PEG compound. (5) DBCO-dPEG®12-TFP ester simplifies the analysis of conjugates formed in the crosslinking reactions because the dPEG® crosslinker is a product with a discrete chain length and a single molecular weight.
DBCO-dPEG®12-TFP ester, PN11366, is one of a series of crosslinkers, each with a different dPEG® chain length, containing DBCO and a TFP ester. To see all of our click chemistry reagents, please click here.
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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.
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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