DBCO-dPEG®₃₆-TFP ester

$300.00 – $1,950.00

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PRODUCT IS SOLD STRICTLY FOR INTERNAL LABORATORY AND RESEARCH PURPOSES ONLY AND HAS NOT BEEN REVIEWED BY THE FDA. PRODUCT IS NOT FOR RESALE AND CANNOT BE INCORPORATED INTO COMMERCIAL GOODS FOR ANY USE OR USED IN THE DEVELOPMENT OF COMMERCIAL PRODUCTS OR IN THE PERFORMANCE OF COMMERCIAL SERVICES UNLESS UNDER A SEPARATE LICENSING, SUPPLY, OR DISTRIBUTOR AGREEMENT WITH QUANTA BIODESIGN, LTD. For information pertaining to the commercial use of our products, please click here to contact us.

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Product#: 10598 Categories: Click Chemistry, Copper-Free Click Crosslinkers

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.

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Frequently Asked Questions (about dPEG^® products)

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:

Bulk Quantities Are Available

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 Edition 2010, 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. Synlett 2017, 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.