DBCO-dPEG®36-TFP ester, product number 10598, is a heterobifunctional, bioorthogonal crosslinker designed to join azides and amines across a long, flexible, hydrophilic spacer. The tetrafluorophenyl (TFP) ester reacts specifically with free amines to form amide bonds, while the dibenzylcyclooctyne (DBCO) moiety selectively forms triazole linkages with azides via a click chemistry reaction known as strain-promoted azide-alkyne cycloaddition (SPAAC). A single molecular weight, discrete polyethylene glycol (dPEG®) spacer separates the two functional groups and imparts hydrophilicity to the crosslinker.
Copper-Free Click Chemistry
Carolyn Bertozzi and coworkers published their discovery of SPAAC, also known as “copper-free click chemistry,” in 2004. This discovery improved the click chemistry toolbox by eliminating toxic copper catalysts, thus permitting the labeling of live cells through a genuinely bioorthogonal reaction. (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 than NHS esters, even at higher pH ranges. Moreover, Quanta BioDesign’s in-house testing shows that at optimum pH, TFP esters label primary amines more readily than NHS esters. Published research by Wang et al. supports this finding. (3)
PEGylation with dPEG® Reagents
Conventional PEG reagents are dispersed (properly, non-uniform) 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 polymerization. Thus, our dPEG® products are monodispersed (Ð = 1). Our dPEG® linkers simplify the analysis of complex biological and biochemical constructs because each dPEG® crosslinker has a discrete chain length and single molecular weight.
Please don’t hesitate to contact us for a quote if you need bulk products in larger package sizes than our standard ones. Our commercial capabilities permit us to manufacture this product at any scale you need.
Buy It Now!
Please click the “Add to Cart” button to get started with your order!
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.
Necessary cookies are absolutely essential for the website to function properly. This category only includes cookies that ensures basic functionalities and security features of the website. These cookies do not store any personal information.
Any cookies that may not be particularly necessary for the website to function and is used specifically to collect user personal data via analytics, ads, other embedded contents are termed as non-necessary cookies. It is mandatory to procure user consent prior to running these cookies on your website.