Specs:

 SDS

Molecular Weight: 505.63; single compound

CAS: 756525-97-0

Purity: > 98%

Spacers: dPEG® Spacer is 18 atoms and 20.6 Å

Shipping: Ambient

References: Greg T. Hermanson, Bioconjugate Techniques, 2nd Edition, Elsevier Inc., Burlington, MA 01803, April, 2008 (ISBN-13: 978-0-12-370501-3; ISBN-10: 0-12-370501-0); See pp. 733-736 for a general discussion of the chemistry and a general protocol for labeling of glycoprotein is given on p. 736.

Greg T. Hermanson, Bioconjugate Techniques, 3rd Edition, Elsevier, Waltham, MA 02451, 2013, ISBN 978-0-12-382239-0; See Chapter 18, Discrete PEG Reagents, pp. 787-821, for a full overview of the dPEG® products.

Development of biosensor-based assays to identify anti-infective oligosaccharides. Jonathan A. Lane, Raj K. Mehra, Stephen D. Carrington, Rita M. Hickey. Analytical Biochemistry. 2011, 410 (2) pp 200-205. November 25, 2010. DOI: 10.1016/j.ab.2010.11.032.

Chemical labelling of active serum thioester proteins for quantification. Lotta Holm, Gareth L. Ackland, Mark R. Edwards, Ross A. Breckenridge, Robert B. Sim, John Offer. Immunbiology. 2010, 2017 (2) 256-264. July 18, 2011. DOI :10.1016/j.imbio.2011.07.021.

Electrochemically Directed Modification of ITO Electrodes and Its Feasibility for the Immunosensor Development. Daegeun Yu and Kyuwon Kim. Bull Korean Chem. Soc.2009, 30 (4) pp 955-958. February 23, 2009.

WSS25 Inhibits Growth of Xenografted Hepatocellular Cancer Cells in Nude Mice by Disrupting Angiogenesis via Blocking Bone Morphogenetic Protein (BMP)/Smad/Id1 Signaling. Hong Qiu, Bo Yang, Zhi-Chao Pei, Zhang Zhang and Kan Ding. JBC. 2010, 285 (42) pp 32638–32646. October 15, 2010. DOI: 10.1074/jbc.M110.105544.

Transcription Termination Factor Rho Can Displace Streptavidin from Biotinylated RNA. Annie Schwartz, Emmanuel Margeat, A. Rachid Rahmouni, and Marc Boudvillain. JBC. 2007, 282 (43) pp 31469–31476. October 26, 2007. DOI: 10.1074/jbc.M706935200.

Comparing the efficiencies of hydrazide labels in the study of protein carbonylation in human serum albumin. Zafer Ugur & Chelsea M. Coffey & Scott Gronert. Analytical and Bioanalytical Chemistry. 2012, 404 (5) pp 1399-1411. July 19, 2012. DOI: 10.1007/s00216-012-6235-9.

Simultaneous Monitoring of Presynaptic Transmitter Release and Postsynaptic Receptor Trafficking Reveals an Enhancement of Presynaptic Activity in Metabotropic Glutamate Receptor-Mediated Long-Term Depression. Wei Xu, Yiu Chung Tse, Frederick A. Dobie, Michel Baudry, Ann Marie Craig, Tak Pan Wong, and Yu Tian Wang. The Journal of Neuroscience. 2013, 33 (13) pp 5867-5877. March 27, 2013. DOI:10.1523/JNEUROSCI.1508-12.2013.

Three Recombinant Engineered Antibodies against Recombinant Tags with High Affinity and Specificity. Hongyu Zhao, Ao Shen, Yang K. Xiang, and David P. Corey. PLoS ONE. 2016, 11 (3) e0150125. March 4, 2016. DOI: 10.1371/journal.pone.0150125.

The carbohydrate-linked phosphorylcholine of the parasitic nematode product ES-62 modulates complement activation. Umul Kulthum Ahmed, N. Claire Maller, Asif J. Iqbal, Lamyaa Al-Riyami, William Harnett, and John G. Raynes. The Journal of Biological Chemistry. 2016, April 4, 2016. DOI: 10.1074/jbc.M115.702746.

A Facile Approach to Functionalize Cell Membrane-Coated Nanoparticles. Hao Zhou, Zhiyuan Fan, Pelin K. Lemons, and Hao Cheng. Theranostics. 2016, 6 (7) pp 1012-1022. April 28, 2016. DOI: 10.7150/thno.15095.

Epidermal-specific deletion of CD44 reveals a function in keratinocytes in response to mechanical stress. M Shatirishvili, AS Burk, CM Franz, G Pace, T Kastilan, K Breuhahn, E Hinterseer, A Dierich, L Bakiri, EF Wagner, H Ponta, TN Hartmann, M Tanaka, and V Orian-Rousseau. Cell Death and Disease. 2016, 7 (e2461). November 10, 2016. DOI: 10.1038/cddis.2016.342.

Antibody neutralization of CXCL10 in vivo is dependent on binding free and not endothelial bound chemokine: Implications for the design of a new generation of anti-chemokine therapeutic antibodies. Pauline Bonvin, Franck Gueneau, Vanessa Buatois, Maud Charreton-Galby, Stanley Lasch, Marie Messmer, Urs Christen, Andrew D Luster, Zoe Johnson, Walter Ferlin, Marie Kosco-Vilbois, Amanda Proudfoot, and Nicolas Fischer. The Journal of Biological Chemistry. 2017, 292 (10), pp 4185-4197. January 30, 2017. DOI: 10.1074/jbc.M116.745877.

The Migrastatin Family:  Discovery of Potent Cell Migration Inhibitors by Chemical Synthesis. Christoph Gaul, Jón T. Njardarson, Dandan Shan, David C. Dorn, Kai-Da Wu, William P. Tong, Xin-Yun Huang, Malcolm A. S. Moore, and Samuel J. Danishefsky. Journal of the American Chemical Society. 2004, 126 (36) pp 11326-11337. DOI: 10.1021/ja048779q.

Exacerbation of CNS inflammation and neurodegeneration by systemic LPS treatment is independent of circulating IL-1β and IL-6. Carol L Murray, Donal T Skelly, and Colm Cunningham. Journal of Neuroinlfammation. 2011. May 17, 2011. DOI: 10.1186/1742-2094-8-50.

Exploitation of SPR to Investigate the Importance of Glycan Chains in the Interaction between Lactoferrin and Bacteria. Noelle O’Riordan, Michelle Kilcoyne, Lokesh Joshi, and Rita M. Hickey. Senors. 2017, 17 (7) p 115. June 27, 2017. doi:10.3390/s17071515.

Producing A Peptide For Use In A Blood Biosensor For Injury Detection. Errek Manh Trung Pham. Youngstown State University Theses & Dissertations Center. 2020. December 2020. ohiolink.edu/1607519672342672


Additional Search Phrases:

Biotin-dPEG4-hydrazide, 756525970, PEG, dPEG, discrete PEG, polyethylene glycol, PEGylation reagent, biotin, biotinylation, biotinylation reagent, biotin labeling, biotin label, hydrazide, hydrazides, hydrazone, hydrazones, cleavable PEG, carbonyl reactive, carboxyl reactive, peptide formation, Biotin-PEG4-hydrazide, Hydrazide-PEG4-Biotin, Biotin-PEG-hydrazide



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Biotin-dPEG®₄-hydrazide

$170.00 – $850.00

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PRODUCT IS SOLD STRICTLY FOR INTERNAL LABORATORY AND RESEARCH PURPOSES ONLY AND HAS NOT BEEN REVIEWED BY THE FDA. PRODUCT IS NOT FOR RESALE AND CANNOT BE INCORPORATED INTO COMMERCIAL GOODS FOR ANY USE OR USED IN THE DEVELOPMENT OF COMMERCIAL PRODUCTS OR IN THE PERFORMANCE OF COMMERCIAL SERVICES UNLESS UNDER A SEPARATE LICENSING, SUPPLY, OR DISTRIBUTOR AGREEMENT WITH QUANTA BIODESIGN, LTD. For information pertaining to the commercial use of our products, please click here to contact us.

Email Sales@QuantaBioDesign.com for Bulk Pricing and Custom Syntheses
Product#: 10219 Categories: ,

Biotin-dPEG®4-hydrazide, product number 10219, is a popular offering from Quanta BioDesign, Ltd. The amphiphilic spacer provides excellent water solubility for the biotin group. The water-soluble dPEG®4 spacer is longer than the hydrophobic aminocaproic acid (LC) spacer used in biotin-LC-hydrazide. Moreover, the dPEG®4 spacer reduces or eliminates non-specific binding in many applications.

Conventional Biotinylation Reagents Compared to Biotin-dPEG®4-hydrazide

For a general discussion of biotinylation with dPEG® products, please visit our page “Biotinylation with dPEG® Products.” To learn more about Quanta BioDesign’s dPEG® technology, please click here. To find answers to the questions that we are most frequently asked, please click this link.

Biotinylation is the process of covalently attaching biotin to a molecule such as a peptide, protein, or nucleic acid, or a surface such as glass or gold. Bioconjugation research and product development use biotin extensively. Biotin is poorly soluble in water. However, the amphiphilic dPEG® linker imparts excellent solubility in aqueous media and organic solvents. Traditionally, biotin-hydrazide reagents add the hydrazide moiety directly onto the carboxylic acid end of either biotin or LC-biotin (biotin coupled to aminocaproic acid). These constructs are quite hydrophobic. Therefore, dissolution in an organic solvent (typically DMSO) is required to use them. Their hydrophobic nature can trigger rapid aggregation of biotinylated molecules, especially proteins.

The dPEG®4 spacer in Biotin-dPEG®4-hydrazide is amphiphilic. The ability to use Biotin-dPEG®4-hydrazide directly in water or aqueous buffer makes it more compatible with biological molecules than LC-biotin. Also, this product will not trigger aggregation due to hydrophobicity issues. Indeed, it reduces non-specific binding between biotin and biomacromolecules. A crosslinker’s hydrophobicity often triggers non-specific binding.

Using Biotin-dPEG®4-hydrazide in Bioconjugation

Biotin-dPEG®4-hydrazide is a carbonyl-reactive compound that forms semi-permanent hydrazone bonds with aldehydes, ketones, and carboxylic acid groups. Although there are numerous natural small molecules containing aldehydes and ketones, macromolecules of biological importance (peptides, proteins, and nucleic acids) rarely contain them. However, glycosylated proteins such as antibodies frequently contain carbohydrate residues known as reducing sugars that can be oxidized with sodium periodate, neuraminidase, or galactose oxidase to form aldehydes.

The aldehydes thus formed then can be reacted with Biotin-dPEG®4-hydrazide at pH 6.0 – 6.0, labeling the protein with biotin through the formation of a Schiff base. Aniline or para-phenylenediamine catalyzes the reaction, forming the Schiff base quickly. For additional bond stability, sodium cyanoborohydride can be used to reduce the Schiff base to a secondary amine. Via carbodiimide chemistry (for example, 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide, also known as EDC), Biotin-dPEG®4-hydrazide reacts with carboxylic acid groups forming a stable bond.

Biotin-dPEG®4-hydrazide is highly useful for installing a biotin label onto glycoproteins. It is also used in cell labeling to label glycoproteins on cell surfaces. Biotinylated glycoproteins can be identified using streptavidin-horseradish peroxidase (HRP) conjugates, because of the high affinity between biotin and streptavidin. Biotinylated secondary antibodies are used frequently with streptavidin in plate-based assays such as ELISA and western blots. This reagent, coupled with avidin that has been modified to have reduced biotin-binding affinity, is for affinity purification of molecules.

Oxyamine Alternatives to Biotin-dPEG®4-hydrazide

Compounds functionalized with oxyamine also form bonds with aldehydes and ketones. These bonds are called “oxime bonds.” Oxime bonds are more stable than hydrazone bonds at low pH. Consequently, biotin functionalized with oxyamine may be preferable to Biotin-dPEG®4-hydrazide in some applications. Quanta BioDesign offers products with the oxyamine functional group as an alternative to Biotin-dPEG®4-hydrazide. If you are interested in these compounds, please click here.

Commercial Scale Production Is Available for Biotin-dPEG®4-hydrazide

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.

Act Now

Stop using inferior biotinylation reagents! Sure, many other people use LC-biotin products, but you can do better. Our biotinylation reagents offer water solubility, improved hydrodynamic volume, no background noise (which means better signal), and no protein precipitation caused by aggregation. Why would you not use something better?

To get started with better biotinylation reactions, click the “Add to Cart” button now. You will not regret it.

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Additional information

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

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