Azido-dPEG®8-acid, product number 10512, is a click chemistry reagent. The azide moiety on one end of the molecule can be used for copper(I)-catalyzed click chemistry or copper free click chemistry. Between the azide moiety and the propanoic acid moiety on the other end of the molecule is a single molecular weight, discrete polyethylene glycol (dPEG®) spacer. The propanoic acid moiety can be coupled to a primary or secondary amine by an acylation reaction.
Click chemistry enables rapid, chemoselective, stereospecific reactions between an azide and an alkyne leading to the formation of a triazole ring joining the two reacted molecules. Since its publication in 2001 by K. Barry Sharpless and colleagues, click chemistry has grown consistently in popularity and importance for the development of new chemical structures. The first-reported click chemistry reactions were catalyzed by copper(I) and are known as Cu(I)-catalyzed azide alkyne cycloaddition (CuAAC). Subsequently, copper free click chemistry (formally known as strain promoted azide alkyne cycloaddition, or SPAAC) was developed so as to facilitate click chemistry reactions in living cells without the use of toxic copper salts. For more information, please see Click Chemistry with dPEG® Reagents.
Activation of the propanoic acid moiety with an acylating agent enables conjugation of azido-dPEG®8-acid to a primary or secondary amine. Popular acylating agents include such as N-hydroxysuccinimide (NHS); 2,3,5,6-tetrafluorophenol (TFP); or 2,3,4,5,6-pentafluorophenol (PFP). Alternatively, 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) or another suitable carbodiimide can be used to couple the acid moiety directly to an amine without prior activation.
Quanta BioDesign’s dPEG® products are single molecular weight products. Unlike traditional, polymeric polyethylene glycol (PEG), dPEG® products contain a single molecular weight PEG chain with a discrete chain length. Put another way, a dPEG® is a single product, not a polymer. The use of dPEG® instead of traditional polymer PEG allows accurate characterization of conjugates without sacrificing any of the benefits of PEG. To learn more about Quanta BioDesign’s dPEG® technology, please click here. To read answers to our frequently asked questions, please click this link.
Quanta BioDesign offers numerous click chemistry reagents, including a broad array of azide-functionalized dPEG® products and dPEG® products functionalized with dibenzyl cyclooctyne (DBCO) for SPAAC. Please click this link to see all of our click chemistry products.
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.
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. Want to learn more about Greg’s book? Click here now for a review of Greg’s book 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, pp 787-838.
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.
Kolb, H. C.; Sharpless, K. B. The growing impact of click chemistry on drug discovery. Drug Disc. Today, 2003, 8(24), 1128-1137.
Baskin, J. M.; Bertozzi, C. R. Bioorthogonal Click Chemistry: Covalent Labeling in Living Systems. QSAR & Combinatorial Science2007, 26(11–12), 1211–1219. https://doi.org/10.1002/qsar.200740086.
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.
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.
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