Bis-dPEG®11-DBCO, product number 11372, is a click chemistry reagent consisting of two dibenzylcyclooctyne (DBCO) groups separated by a single molecular weight, discrete polyethylene glycol (dPEG®) spacer that is 39 atoms (44.2 Å) long. The total length of the molecule is 55 atoms (67.2 – 68.2 Å) long. The DBCO groups react with azide groups via the bioorthogonal click chemistry reaction known as strain-promoted azide-alkyne cycloaddition (SPAAC), also known as copper-free click chemistry. This product is particularly useful for click chemistry reactions where the presence or use of copper(I) [Cu(I)] is undesirable.
Traditional polyethylene glycol (PEG) is a dispersed polymer consisting of a complex Poisson distribution of different chain lengths and molecular weights that make exact analysis and characterization quite challenging. Quanta BioDesign’s dPEG® products contain precisely defined, single molecular weight, discrete PEG chains (thus the dPEG® trademark). Discrete PEG reagents provide all of the benefits of traditional PEG, including water solubility, increased hydrodynamic volume with consequent protection from renal clearance, reduced or eliminated aggregation, and reduced or eliminated immunogenicity. Discrete PEG reagents also remove the analytical complications that result from the presence of an often-large distribution of PEG oligomers found in traditional polymer PEG reagents.
The DBCO functional groups at each end of the dPEG® spacer consist of a strained cyclooctyne ring with two benzyl rings fused on either side of the central cyclooctyne ring. A glutaric acid group extends from the nitrogen atom on the cyclooctyne ring to permit conjugation to terminal amine groups on the dPEG® spacer. DBCO is a bioorthogonal, copper-free click chemistry reagent that reacts with azide groups through strain on the cyclooctyne ring, hence the acronym SPAAC. The SPAAC reaction produces a triazole ring fused to the eight-sided ring, with corresponding changes in bond hybridization. SPAAC is useful for reactions where Cu(I) cannot be used due to toxicity issues (for example, with living cells) or for reactions where copper would be difficult to remove in the workup of the product. For more information, please see Click Chemistry with dPEG® Reagents.
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If you need bulk product in a larger package size than our standard sizes, please contact us for a quote. Our commercial capabilities permit us to manufacture this product at any scale that you need.
Hermanson, G. T. Chapter 17, Chemoselective Ligation; Bioorthogonal Reagents. Bioconjugate Techniques, 3rd edition. Academic Press: New York, 2013, pp 757-786, particularly pages 769-775, discussing click chemistry. Want to read a review of Greg’s book or purchase a copy? Click here now!
Hermanson, G. T. Chapter 18, PEGylation and Synthetic Polymer Modification. Bioconjugate Techniques, 3rd edition. Academic Press: New York, 2013, pp 787-838.
Baskin, J. M.; Bertozzi, C. R. Bioorthogonal Click Chemistry: Covalent Labeling in Living Systems. QSAR & Combinatorial Science2007, 26(11–12), 1211–1219. https://doi.org/10.1002/qsar.200740086.
4. Dommerholt, J.; Rutjes, F. P. J. T.; van Delft, F. L. Strain-Promoted 1,3-Dipolar Cycloaddition of Cycloalkynes and Organic Azides. Top. Curr. Chem. (Z)2016, 374(2), 16. https://doi.org/10.1007/s41061-016-0016-4
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