Bromoacetamido-dPEG®₁₂-amido-DBCO

Bromoacetamido-dPEG®12-amido-DBCO, product number 11223, combines a thiol-reactive bromoacetyl group with dibenzylcyclooctyne (DBCO, also known as DIBAC), a reactive group for strain promoted azide alkyne cycloaddition. The two reactive groups are joined through a medium-length, flexible, single molecular weight, discrete polyethylene glycol (dPEG®) linker.

Traditional PEG is a polymer consisting of an intractable mixture of different chain lengths and molecular weights in a Poisson distribution. However, each of Quanta BioDesign's PEG products consists of a single molecular weight of PEG with a discrete chain length, hence the tradename dPEG®. Quanta BioDesign developed the processes for manufacturing dPEG® and has been the world leader in dPEG® research, development, and manufacturing since our founding in 1999.

The bromoacetyl group reacts chemoselectively with thiols at pH ≥ 8.0, in contrast to the maleimide group {link}, which reacts chemoselectively with sulfhydryls within the range of pH 6.5 – 7.5. The DBCO moiety is a strained cyclooctyne ring with two fused benzyl rings on either side of the cyclooctyne ring. An aminopropionic acid unit extends from a ring nitrogen atom to provide a means of coupling the DBCO to the dPEG® linker. DBCO was designed for strain promoted azide alkyne cycloaddition (SPAAC), also known as copper free click chemistry. DBCO was developed by building on the work of Carolyn Bertozzi and colleagues who developed SPAAC for bio-orthogonal click chemistry applications.

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.

Application References:

Hermanson, G. T. Chapter 6, Heterobifunctional Crosslinkers. Bioconjugate Techniques, 3rd edition. Academic Press, New York: 2013, pp. 299 – 339. See page 311 discussing the reactivity of the bromoacetyl group.
Hermanson, G. T. Chapter 18, PEGylation and Synthetic Polymer Modification. Bioconjugate Techniques, 3rd edition. Academic Press, New York: 2013, pp 787 – 838.
Schelté, Philippe; Boeckler, C.; Frisch, B.; Schuber, F. Differential Reactivity of Maleimide and Bromoacetyl Functions with Thiols: Application to the Preparation of Liposomal Diepitope Constructs. Bioconjugate Chem. 2000, 11(1), 118–123. https://doi.org/10.1021/bc990122k.
Rosen, B. M.; Lligadas, G.; Hahn, C.; Percec, V. Synthesis of Dendrimers through Divergent Iterative Thio-Bromo “Click” Chemistry. Journal of Polymer Science Part A: Polymer Chemistry 2009, 47(15), 3931–3939. https://doi.org/10.1002/pola.23519.
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.
Patterson, D. M.; Nazarova, L. A.; Prescher, J. A. Finding the Right (Bioorthogonal) Chemistry. ACS Chem. Biol. 2014, 9(3), 592–605. https://doi.org/10.1021/cb400828a.
Baskin, J. M.; Bertozzi, C. R. Bioorthogonal Click Chemistry: Covalent Labeling in Living Systems. QSAR & Combinatorial Science 2007, 26(11–12), 1211–1219. https://doi.org/10.1002/qsar.200740086.

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