Biotin Hydrazide – VectorLabs https://staging.vectorlabs.com From linker design and synthesis, bioconjugated design and manufacturing, biomolecule labeling and functionalization, and detection system and solutions, our team is here to help you move forward, with impact. Wed, 22 Oct 2025 17:16:35 +0000 en-US hourly 1 https://wordpress.org/?v=6.8.3 https://staging.vectorlabs.com/wp-content/uploads/2024/11/V-favicon-02-100x100.png Biotin Hydrazide – VectorLabs https://staging.vectorlabs.com 32 32 Biotin-dPEG®₄-hydrazide https://staging.vectorlabs.com/products/biotin-dpeg4-hydrazide/ Sat, 24 Feb 2024 02:07:16 +0000 https://staging.vectorlabs.com/?post_type=product&p=35457 Biotin-dPEG®4-hydrazide, product number QBD-10219, is a hydrophilic biotinylation reagent designed for labeling the carbohydrate coats of glycoproteins with biotin. The amphiphilic spacer provides excellent water solubility for poorly water-soluble biotin. Moreover, the dPEG®4 spacer is longer than the hydrophobic aminocaproic acid (LC) spacer used in biotin-LC-hydrazide, so it provides somewhat better access to the biotin binding pockets of avidin and streptavidin. Additionally, the dPEG®4 spacer reduces or eliminates non-specific binding in many applications.

Biotin-dPEG®4-hydrazide, QBD-10219, 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 5 – 7, 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.

The amphiphilic dPEG®4 spacer in Biotin-dPEG®4-hydrazide provides the ability to use Biotin-dPEG®4-hydrazide directly in water or aqueous buffer, making it more biocompatible than LC-biotin. Moreover, QBD-10219 will not trigger protein or peptide aggregation or cause non-specific binding due to hydrophobicity issues from the linker, both of which can occur with traditional biotin linkers like LC-biotin.

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 avidin or 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.

Specifications

Unit Size 50 mg, 1000 mg
Molecular Weight 505.63; single compound
Chemical formula C₂₁H₃₉N₅O₇S
CAS 756525-97-0
Purity > 98%
Spacers dPEG® Spacer is 18 atoms and 20.6 Å
Shipping Ambient
Typical solubility properties (for additional information contact Customer Support) DMAC, DMSO or water; it is not soluble in acetonitrile.
Storage and handling -20°C; Always let come to room temperature before opening; be careful to limit exposure to moisture and restore under an inert atmosphere; stock solutions can be prepared with dry solvent and kept for several days (freeze when not in use). dPEG® pegylation compounds are generally hygroscopic and should be treated as such. This will be less noticeable with liquids, but the solids will become tacky and difficult to manipulate, if care is not taken to minimize air exposure.

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Description

Biotin-dPEG®4-hydrazide, product number QBD-10219, is a hydrophilic biotinylation reagent designed for labeling the carbohydrate coats of glycoproteins with biotin. The amphiphilic spacer provides excellent water solubility for poorly water-soluble biotin. Moreover, the dPEG®4 spacer is longer than the hydrophobic aminocaproic acid (LC) spacer used in biotin-LC-hydrazide, so it provides somewhat better access to the biotin binding pockets of avidin and streptavidin. Additionally, the dPEG®4 spacer reduces or eliminates non-specific binding in many applications.

Biotin-dPEG®4-hydrazide, QBD-10219, 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 5 – 7, 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.

The amphiphilic dPEG®4 spacer in Biotin-dPEG®4-hydrazide provides the ability to use Biotin-dPEG®4-hydrazide directly in water or aqueous buffer, making it more biocompatible than LC-biotin. Moreover, QBD-10219 will not trigger protein or peptide aggregation or cause non-specific binding due to hydrophobicity issues from the linker, both of which can occur with traditional biotin linkers like LC-biotin.

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 avidin or 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.

Specifications

Unit Size50 mg, 1000 mg
Molecular Weight505.63; single compound
Chemical formulaC₂₁H₃₉N₅O₇S
CAS756525-97-0
Purity> 98%
SpacersdPEG® Spacer is 18 atoms and 20.6 Å
ShippingAmbient
Typical solubility properties (for additional information contact Customer Support)DMAC, DMSO or water; it is not soluble in acetonitrile.
Storage and handling-20°C; Always let come to room temperature before opening; be careful to limit exposure to moisture and restore under an inert atmosphere; stock solutions can be prepared with dry solvent and kept for several days (freeze when not in use). dPEG® pegylation compounds are generally hygroscopic and should be treated as such. This will be less noticeable with liquids, but the solids will become tacky and difficult to manipulate, if care is not taken to minimize air exposure.

Documents

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

The post Biotin-dPEG®₄-hydrazide appeared first on VectorLabs.

]]> Biotin (Long Arm) Hydrazide https://staging.vectorlabs.com/products/biotin-long-arm-hydrazide/ Sat, 29 Apr 2023 02:57:16 +0000 https://staging.vectorlabs.com/?post_type=product&p=13285 Description

Biotin (Long Arm) Hydrazide (SP-1100) reacts with aldehyde groups and thus can be used to label carbohydrate groups present in a wide variety of macromolecules. The spacer arm in this product allows optimal accessibility of avidin or streptavidin conjugates to biotin.

Features:

  • Can be incorporated into RNA at the 3′ end (after oxydation or 3′ ribose)

Specifications

Unit Size 50 mg
Target for Labeling Carbohydrate, RNA
Recommended Storage 2-8 °C (desiccated). Once in solution, store frozen.
Molecular Weight 371.5
Chemical Formula C16H29N5O3S
Tag/Group Incorporated Biotin
Safety Title WARNING: NA – www.P65Warnings.ca.gov

The post Biotin (Long Arm) Hydrazide appeared first on VectorLabs.

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Description

Biotin (Long Arm) Hydrazide (SP-1100) reacts with aldehyde groups and thus can be used to label carbohydrate groups present in a wide variety of macromolecules. The spacer arm in this product allows optimal accessibility of avidin or streptavidin conjugates to biotin.

Features:

  • Can be incorporated into RNA at the 3′ end (after oxydation or 3′ ribose)

Specifications

Unit Size50 mg
Target for LabelingCarbohydrate, RNA
Recommended Storage2-8 °C (desiccated). Once in solution, store frozen.
Molecular Weight371.5
Chemical FormulaC16H29N5O3S
Tag/Group IncorporatedBiotin
Safety TitleWARNING: NA – www.P65Warnings.ca.gov

Documents

Citations

Technical Information

Polysaccharides, glycoproteins, or glycolipids

Biotin can be incorporated into viruses, bacteria, or animal and plant cells via their surface carbohydrate groups.

Incorporation of Biotin (Long Arm) Hydrazide occurs onto sugars containing unsubstituted vicinal hydroxyl groups that are usually present at the non-reducing termini of the oligosaccharide.

Coupling of biotin is accomplished in two steps:

  1. A brief treatment of the saccharide with periodate (not included) produces aldehyde groups on the sugars containing unsubstituted vicinal hydroxyl groups.
  2. Biotin (Long Arm) Hydrazide reacts with the aldehyde groups, producing a stable linkage between the saccharide and biotin.

RNA 3’End Labeling

RNA can be specifically labeled with biotin at the 3′ end. The two-step procedure involves:

  1. Mild oxidation of the ribose located at the 3′ end of RNA, the only ribose susceptible to periodate oxidation. The bond between the 2 and 3 hydroxyl groups on the ribose is cleaved, generating two aldehyde groups.
  2. Reaction of both aldehyde groups with Biotin (Long Arm) Hydrazide, introducing two biotins at the 3 end.

Proteins and other molecules

This reagent can also be used to couple biotin to carboxyl groups on proteins and other molecules using a carbodiimide coupling method.

Other materials

Initial activation of a material such as plastics with glutaraldehyde allows subsequent incorporation of Biotin (Long Arm) Hydrazide onto the surface.

BiotinHydrazide jpg

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