References: Greg T. Hermanson, Bioconjugate Techniques, 2nd Edition, Elsevier Inc., Burlington, MA 01803, April, 2008 (ISBN-13: 978-0-12-370501-3; ISBN-10: 0-12-370501-0). Specifically see pp. 726-729 in his Chapter 18 on discrete PEG compounds for pegylation applications.
Greg T. Hermanson, Bioconjugate Techniques, 3rd Edition, Elsevier, Waltham, MA 02451, 2013, ISBN 978-0-12-382239-0; See chapter 18, Discrete PEG Reagents, pp.787-821, for a full overview of the dPEG® products.
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.
DBCO-dPEG®36-TFP ester, PN10598, is one of a series of crosslinkers, each with a different dPEG® chain length, containing DBCO and a TFP ester. The other products in this series are:
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.
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REFERENCES:
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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