Bis-MAL-Lysine-dPEG®₄-TFP ester

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Bis-MAL-Lysine-dPEG®4-TFP ester, product number 10631, is a unique crosslinker from Quanta BioDesign, Ltd. The alpha (α) and epsilon (ε) amines of lysine are functionalized with sulfhydryl-reactive maleimidopropyl groups. The carboxylic acid tail of lysine is conjugated to a single molecular weight, discrete polyethylene glycol (dPEG®) spacer containing an amine-reactive 2,3,5,6-tetrafluorophenyl (TFP) ester. The distance from the carbonyl carbon of the dPEG® spacer to the reactive site of the α-amine-conjugated maleimide group is 25 atoms (18.773 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 (26.105 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 uniform conjugates. 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.

TFP Esters and NHS Esters Compared

TFP esters react with primary and secondary amines to form stable amide bonds like the more widely used N-hydroxysuccinimidyl (NHS) esters. However, TFP esters demonstrate superior hydrolytic stability and higher reactivity with amines than NHS esters. For more information about the benefits of using TFP esters, please see TFP Esters Have More Hydrolytic Stability and Greater Reactivity than NHS Esters.

Using Bis-MAL-Lysine-dPEG®4-TFP ester

By design, the two maleimide groups of Bis-MAL-Lysine-dPEG®4-TFP ester 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.

For more information about maleimide chemistry and reactivity, please read Maleimide Reaction Chemistry.

The TFP ester end of the molecule reacts with free amines to form stable amide bonds. The optimum pH for this reaction is 7.5 – 8.0. Thus, the product functions as a crosslinker. Possible uses for Bis-MAL-Lysine-dPEG®4-TFP ester include the construction of antibody-drug conjugates (ADCs); immobilization of antibodies or antibody fragments on solid supports; and dimerization of sulfhydryl-containing peptides followed by crosslinking to an amine-modified surface.

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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Application References:

  1. 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. Click here now for a review of Greg’s book and a link to purchase it.
  2. Hermanson, G. T. Chapter 18, PEGylation and Synthetic Polymer Modification. Bioconjugate Techniques, 3rd edition. Academic Press: New York, 2013, pages 787 – 838.
  3. 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.

Additional information

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