Bis-MAL-Lysine-dPEG®4-acid, product number 10630, is a unique crosslinker from Quanta BioDesign, Ltd. The two amines of lysine are functionalized with maleimidopropyl groups that react with sulfhydryl groups. The carboxylic acid tail of lysine is conjugated to a single molecular weight, discrete polyethylene glycol (dPEG®) spacer containing a carboxylic acid terminus that can be reacted with free amines or used to provide negative surface charge. The distance from the carbonyl carbon of the dPEG® spacer to the reactive site of the α-amine-conjugated maleimide group is 25 atoms (17.5 Å) long. The distance from the carbonyl carbon of the dPEG® spacer to the reactive site of the ε-amine-conjugated maleimide group is 29 atoms (27.9 Å) long.
PEGylation with dPEG® Products
Unlike traditional polyethylene glycol (PEG), which is a disperse polymer (Ð > 1), all of Quanta BioDesign’s dPEG® products are synthesized as single molecules. Consequently, our dPEG® products create conjugates with no dispersity. These conjugates exhibit a more straightforward analysis compared to traditional polymer PEG products. For more information about dPEG® products, please visit this page. To get answers to frequently asked questions, please click here.
By design, the two maleimide groups of Bis-MAL-Lysine-dPEG®4-acid can be used to bridge disulfides. For example, this capability may be useful in antibodies following reduction of the disulfide groups. Moreover, the two maleimide groups can be used to dimerize small molecules or peptides, each of which possesses a single free thiol group.
At pH 6.5 – 7.5, maleimide groups react chemoselectively with sulfhydryls. However, above pH 7.5, chemoselectivity is lost, as maleimide groups also will react with free amines.
The carboxylic acid end of the molecule couples with free amines using EDC chemistry to form stable amide bonds. However, if the acid terminus of the molecule is left unreacted, the acid can act as a charge modifier for the molecule to which it is conjugated. Construction of antibody-drug conjugates (ADCs); immobilization of antibodies and antibody fragments; and dimerization of sulfhydryl-containing peptides are some of the possible uses for this product.
Commercial Scale Production
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.
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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. Want to learn more about Greg’s book? Click here now for a review of this remarkable reference work and a link to purchase it.
Hermanson, G. T. Chapter 18, PEGylation and Synthetic Polymer Modification. Bioconjugate Techniques, 3rd edition. Academic Press: New York, 2013, pages 787 – 838.
Kim, T. H.; Jiang, H. H.; Lee, S.; Youn, Y. S.; Park, C. W.; Byun, Y.; Chen, X.; Lee, K. C. Mono-PEGylated Dimeric Exendin-4 as High Receptor Binding and Long-Acting Conjugates for Type 2 Anti-Diabetes Therapeutics. Bioconjugate Chem.2011, 22(4), 625–632. https://doi.org/10.1021/bc100404x.