Biotin-dPEG®₁₂-DBCO

Biotin-dPEG®12-DBCO, product number 11811, labels azide-containing target molecules bioorthogonally using strain-promoted azide-alkyne cycloaddition (SPAAC), also known as "copper-free click chemistry." A linear, single molecular weight, discrete polyethylene glycol (dPEG®) spacer separates the biotin and dibenzylcyclooctyne (DBCO) groups on either end of the molecule. The DBCO functional group reacts with any available azide moiety on a target molecule via SPAAC. The amphiphilic dPEG® spacer imparts water solubility to the product.

Biotinylation
The covalent addition of biotin to a molecule (biotinylation) is one of the most common methods of labeling molecules, such as proteins and peptides, for protein capture, affinity purification, pull-down assay, immunoprecipitation, and enzyme-linked immunosorbent assay (ELISA). The binding affinity of biotin for avidin or streptavidin is one of the strongest known non-covalent bonds. Biotin usually is poorly soluble in water, but the addition of amphiphilic polyethylene glycol (PEG) imparts water solubility to biotin.

Copper-Free Click Chemistry (aka, SPAAC)
Carolyn Bertozzi and coworkers developed SPAAC (copper-free click chemistry) as an alternative to the copper-catalyzed azide-alkyne cycloaddition (CuAAC) developed by K. Barry Sharpless and coworkers. SPAAC avoids the use of copper, which is toxic to living cells. Thus, SPAAC is considered a bioorthogonal reaction that can label living cells. Azides are generally not present in biomolecules, but several methods exist for introducing azide groups into them. The combination of SPAAC via Biotin-dPEG®12-DBCO, PN11811, with azides introduced into biomolecules, allows the user a high degree of control over the labeling process.

Traditional PEG products are dispersed polymers (Đ > 1), consisting of a Poisson distribution of various chain lengths, each with a different molecular weight. Each of Quanta BioDesign's discrete PEG (dPEG®) products contains a single PEG chain length with one molecular weight (Đ = 1). Our dPEG® products are much simpler to analyze than traditional PEG products because our products do not contain the complex mixture of PEG chains found in traditional PEG products.

Application References:

Hermanson, Greg T. Bioconjugate Techniques, 3rd edition. Academic Press, London, 2013.
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 Science 2007, 26(11–12), 1211–1219.
Beatty, K. E.; Fisk, J. D.; Smart, B. P.; Lu, Y. Y.; Szychowski, J.; Hangauer, M. J.; Baskin, J. M.; Bertozzi, C. R.; Tirrell, D. A. Live-Cell Imaging of Cellular Proteins by a Strain-Promoted Azide–Alkyne Cycloaddition. ChemBioChem 2010, 11(15), 2092–2095.
Robinson, P. V.; de Almeida-Escobedo, G.; de Groot, A. E.; McKechnie, J. L.; Bertozzi, C. R. Live-Cell Labeling of Specific Protein Glycoforms by Proximity-Enhanced Bioorthogonal Ligation. J. Am. Chem. Soc. 2015, 137(33), 10452–10455.
Zheng, M.; Zheng, L.; Zhang, P.; Li, J.; Zhang, Y. Development of Bioorthogonal Reactions and Their Applications in Bioconjugation. Molecules 2015, 20(2), 3190–3205.

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