DBCO-dPEG®₂₄-MAL

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DBCO-dPEG®24-MAL, product number 10594, is a long, versatile discrete polyethylene glycol (dPEG®) crosslinking reagent. The dibenzylcyclooctyne (DBCO) moiety permits strain promoted azide-alkyne cycloaddition (SPAAC), also known as “copper free click chemistry.” The maleimidopropyl (MAL) functional group forms a thiol-ether linkage with sulfhydryl groups. The long, 76-atom single molecular weight dPEG® spacer is hydrophilic and non-immunogenic. The crosslinker distance is 90 atoms (99.8Å) from end to end (including the functional groups).

Quanta BioDesign’s dPEG® products clearly differ from traditional, polymeric polyethylene glycol (PEG). Traditional PEG is a disperse polymer product with a Poisson distribution of chain lengths and molecular weights. The intractable mixture of chain lengths and molecular weights in traditional PEG products creates significant analytical challenges. In contrast, Quanta BioDesign’s dPEG® products are single molecular weight compounds. Each dPEG® product contains a single, discrete chain length and is a single, molecular weight. Using Quanta BioDesign’s products greatly simplifies analysis of dPEG®-conjugated compounds. Click here to learn more about our dPEG® technology. Click here to find answers to our most frequently asked questions.

The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) discovered by K. Barry Sharpless and coworkers is one of the best known click chemistry reactions. However, copper toxicity makes this reaction problematic for in vivo labeling experiments. Carolyn Bertozzi and coworkers developed SPAAC as a way to avoid copper’s toxic effects on living cells using highly strained cyclooctyne. Developments since the initial publication show that reagents based on DBCO provide excellent, highly selective reactivity with azides, forming a triazole product.

Maleimide groups are widely popular for their ability to react rapidly with sulfhydryl groups via a Michael addition to form thioether bonds. The resulting thiosuccinimide is stable, though it can reverse slowly over time under physiological conditions. More information about using our maleimide-containing products can be found on our Maleimide Reaction Chemistry page.

DBCO-dPEG®24-MAL provides the benefits of PEG (increased water solubility, non-immunogenicity) without the analytical headaches of PEG dispersity. PN10594 is one of three products with these functional groups, each of which differs by dPEG® chain length. The other two products in this series are PN10592, DBCO-dPEG®4-MAL, and PN10593, DBCO-dPEG®12-MAL. 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:

  1. Hermanson, G. T. Chapter 3, The Reactions of Bioconjugation. Bioconjugate Techniques, 3rd edition. Academic Press: New York, 2013, pp. 229-258, particularly page 241, where maleimide reactions are discussed. Want to know more about Greg’s book? Interested in purchasing your own copy of the book? Click here now for a review of Greg’s book and a link to purchase it.
  2. 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 where click chemistry is discussed.
  3. Hermanson, G. T. Chapter 18, PEGylation and Synthetic Polymer Modification. Bioconjugate Techniques, 3rd edition. Academic Press: New York, 2013, pp 787-838.
  4. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew. Chem. Int. Ed., 2001, 40, 2004-2021.
  5. Kolb, H. C.; Sharpless, K. B. The growing impact of click chemistry on drug discovery. Drug Disc. Today, 2003, 8(24), 1128-1137.
  6. 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.
  7. 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.
  8. 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.

Additional information

Weight .5 oz
Dimensions .75 × .75 × 2 in

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