Bis-MAL-dPEG®₃

Bis-MAL-dPEG®3, product number 10215, is a short, homobifunctional, crosslinking reagent that links two molecules (e.g., peptides, proteins) together via the thiol-maleimide reaction (also known as the thiol-Michael addition). Maleimidopropionate groups functionalize each end of the molecule. A short, single molecular weight, discrete polyethylene glycol (dPEG®) spacer separates the two end groups.

The thiol-maleimide reaction, a type of click chemistry reaction, is a popular way to conjugate molecules. The maleimide functional group rapidly reacts with sulfhydryl groups, and the reaction is chemoselective for sulfhydryls in the pH range of 6.5 – 7.5. The polyethylene glycol (PEG) spacer between the two maleimide groups is a single molecular weight compound with a discrete chain length (thus the tradename dPEG®). This product is not made from a dispersed polymer but is instead a single compound. Applications for this product include mapping which proteins in a complex are close together; determining ligand-receptor binding relationships; and construction of antibody-drug conjugates (ADCs), among many others.

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 3, The Reactions of Bioconjugation. Bioconjugate Techniques, 3rd edition. Academic Press: New York, 2013, pages 229 – 258, particularly page 241, where Greg writes about the maleimide reactive group.
Hermanson, G. T. Chapter 18, PEGylation and Synthetic Polymer Modification. Bioconjugate Techniques, 3rd edition. Academic Press: New York, 2013, pages 787 – 838.
Choe, S. H.; Kim, J. E.; Lee, Y. C.; Jang, Y. J.; Choe, M. H. A Divalent Immunotoxin Formed by the Disulfide Bond between Hinge Regions of Fab Domain. Bulletin of the Korean Chemical Society 2001, 22(12), 1361–1365. http://www.koreascience.or.kr/article/JAKO200113464477984.page
Giron-Monzon, L.; Manelyte, L.; Ahrends, R.; Kirsch, D.; Spengler, B.; Friedhoff, P. Mapping Protein-Protein Interactions between MutL and MutH by Cross-Linking. J. Biol. Chem. 2004, 279(47), 49338–49345. https://doi.org/10.1074/jbc.M409307200.
Pan, H.; Yang, J.; Kopečková, P.; Kopeček, J. Backbone Degradable Multiblock N-(2-Hydroxypropyl)Methacrylamide Copolymer Conjugates via Reversible Addition−Fragmentation Chain Transfer Polymerization and Thiol−ene Coupling Reaction. Biomacromolecules 2011, 12(1), 247–252. https://doi.org/10.1021/bm101254e.
Ravasco, J. M. J. M.; Faustino, H.; Trindade, A.; Gois, P. M. P. Bioconjugation with Maleimides: A Useful Tool for Chemical Biology. Chemistry – A European Journal 2019, 25(1), 43–59. https://doi.org/10.1002/chem.201803174.
Northrop, B. H.; Frayne, S. H.; Choudhary, U. Thiol–Maleimide "Click" Chemistry: Evaluating the Influence of Solvent, Initiator, and Thiol on the Reaction Mechanism, Kinetics, and Selectivity. Polym. Chem. 2015, 6(18), 3415–3430. https://doi.org/10.1039/C5PY00168D.

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