4-formyl-benzamido-dPEG®12-TFP ester, product number 10081, is an aryl aldehyde partner for our hydrazide- and aminooxy-containing products. It is used to introduce an aldehyde into a peptide, protein, or other biomolecules by reacting the 2,3,5,6-tetrafluorophenyl (TFP) ester end with free amines. Reaction with a molecule containing a hydrazide or aminooxy reactive group forms hydrazone or oxime bonds. The single molecular weight, discrete-length polyethylene glycol (dPEG®) spacer is 46 atoms (49.3 Å) long from the carbonyl carbon at the TFP ester end of the molecule to the aryl aldehyde terminus at the opposite end of the molecule.
PEGylation with 4-formyl-benzamido-dPEG®12-TFP ester
Quanta BioDesign’s dPEG® technology creates single molecular weight PEG products with discrete chain lengths. In contrast, traditional PEG reagents are dispersed polymers containing an intractable mixture of different chain lengths of PEG, each chain having a different molecular weight. This dispersity creates significant analytical challenges for users of conventional PEG products. Our dPEG® products provide all of the benefits of traditional PEG products without the accompanying analytical complexity found in dispersed PEG polymers. For more information on our dPEG® technology, please visit our “What is dPEG®?” page. For answers to our most frequently asked questions about dPEG® technology, please click here.
4-formyl-benzamido-dPEG®12-TFP ester is amphiphilic and dissolves in aqueous and organic solvents. Conjugation of the TFP ester end of the molecule should precede crosslinking with a hydrazide or aminooxy compound. The TFP ester reacts with free amines. Effectively, then, 4-formyl-benzamido-dPEG®12-TFP ester converts a free amine to a water-soluble aryl aldehyde. (Click here to read why we at Quanta BioDesign prefer TFP esters over the more common NHS esters.)
Conversion of an amine to an aldehyde in this manner is useful when it is undesirable or impossible to create aldehydes or ketones in biomolecules through sodium periodate oxidation. Moreover, aryl aldehydes are preferable to aliphatic aldehydes, because aryl aldehydes do not freely react with amines in aqueous solution to form a Schiff base. Consequently, spontaneous polymerization or modification of biomolecules will not occur in aqueous media when using 4-formyl-benzamido-dPEG®12-TFP ester.
After installing the aryl aldehyde, the conjugate is available to crosslink with a compound containing a hydrazide or aminooxy reactive group. Greg Hermanson has published protocols for these crosslinking reactions. Also, Quanta BioDesign offers many different dPEG® products containing hydrazide and aminooxy reactive groups that can partner with our aryl aldehyde products. To see the list of potential partners, please click this link.
Commercial Scale Production Is Available for 4-formyl-benzamido-dPEG®12-TFP ester
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.
Hydrophobic crosslinking reagents are sources of problems in bioconjugation chemistry. So, stop using inferior crosslinkers! You can do better. Quanta BioDesign offers dPEG®-based crosslinkers that provide water solubility, improved hydrodynamic volume, no background noise (which means better signal), and no protein precipitation caused by aggregation. Why use anything else?
For crosslinking reactions that are better than you have ever had before, click the “Add to Cart” button now. You will not regret it.
Hermanson, G. T. Chapter 18, PEGylation and Synthetic Polymer Modification. In Bioconjugate Techniques; Academic Press: New York, NY, 2013; pp 787–838. The protocols referenced above are on pages 802 – 806.
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