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Biotin-dPEG®₃-NH₃+TFA- (QBD-10193)

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Biotin-dPEG®3-NH3+TFA– (Biotin-dPEG®3-ammonium trifluoroacetate), product number QBD-10193, is a carboxylate-reactive or carbonyl-reactive biotin-labeling (biotinylation) product offered by Vector Laboratories, Inc. The product reacts with activated esters (N-hydroxysuccinimide, 2,3,5,6-tetrafluorophenyl) of carboxylic acids under mildly basic conditions or couples directly to a carboxylic acid using 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) chemistry. In both cases, stable amide bond linkages are formed. Also, the product can react with carbonyl groups (aldehydes or ketones) to form a Schiff base that can be reduced to a secondary amine using sodium cyanoborohydride if additional conjugate stability is necessary.

Description

Biotin-dPEG®3-NH3+TFA– (Biotin-dPEG®3-ammonium trifluoroacetate), product number QBD-10193, is one of several biotinylation (biotin-labeling) products offered by Vector Laboratories, Inc. The product reacts with activated esters (N-hydroxysuccinimide, 2,3,5,6-tetrafluorophenyl) of carboxylic acids under mildly basic conditions. It can be coupled directly to a carboxylic acid using 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) chemistry. Also, the product can react with carbonyl groups (aldehydes or ketones) to form a Schiff base that can be reduced to a secondary amine using sodium cyanoborohydride if additional conjugate stability is necessary.

Amphiphilic biotin-dPEG®3-NH3+TFA– dissolves equally well in aqueous buffers and organic solvents. Unlike traditional, hydrophobic biotin-labeling products, this product does not need to be dissolved in an organic solvent before being used in an aqueous reaction medium. Furthermore, biotinylation of biomacromolecules with QBD-10193 will not cause aggregation and precipitation. Eliminating aggregation should consequently improve signal-to-noise ratios in applications developed with this product. Reaction with a carboxylic acid or active ester of a carboxylic acid will yield a stable amide bond. Aldehydes are uncommon in biomacromolecules but form by oxidizing reducing sugars in glycosylated proteins. Reactions with aldehydes produce imines that can be reduced under mild conditions to secondary amines with sodium cyanoborohydride.

Any application that can utilize the powerful biotin-avidin/streptavidin affinity can use Biotin-dPEG®3-NH3+TFA–. The terminal amine of QBD-10193 offers the opportunity to biotinylate (1) the carbohydrate coat of glycoproteins and (2) surfaces consisting of carboxylic acids or their active esters. Thus, Biotin-dPEG®3-NH3+TFA– expands the range of molecules and nanoparticles for which dPEG®-biotin is useful.

Specifications

Unit Size100 mg, 1000 mg
Molecular Weight560.63; single compound
Chemical formulaC₂₂H₃₉ F₃N₄O₇ S
CAS1334172-59-6
Purity> 98%
SpacersdPEG® Spacer is 15 atoms and 18.1 Å
ShippingAmbient
Typical solubility properties (for additional information contact Customer Support)Methylene chloride, DMAC, DMSO or water.
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.

References

  1. 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. 529-530 for a general discussion in Greg’s book and on biotinylation as well, as well as pp. 737-738 for a protocol for a compound with just two oxygen. However, other than enhanced solubility and binding distances, the protocol is adaptable to our PN 10193.
  2. 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.
  3. Molecularly Imprinted Polymer Arrays as Synthetic Protein Chips Prepared by Transcription-type Molecular Imprinting by Use of Protein-Immobilized Dots as Stamps. Takahiro Kuwata, Akane Uchida, Eri Takano, Yukiya Kitayama, and Toshifumi Takeuchi. Analytical Chemistry. 2015, 87 (23) pp 11784-11791. November 16, 2015. DOI:10.1021/acs.analchem.5b03134.
  4. Electrogenerated Chemiluminescence. 77. DNA Hybridization Detection at High Amplification with [Ru(bpy)3]­­­2+-Containing Microspheres, Wujian Miao and Allen J. Bard. Anal. Chem. 2004, 76 (18), pp 5379-5386. August 7, 2004. DOI: 10.1021/ac0495236.
  5. Automated flow-through amperometric immunosensor for highly sensitive and on-line detection of okadaic acid in mussel sample. Rocio B. Dominguez, Akhtar Hayat, Audrey Sassolas, Gustavo A. Alonso, Roberto Munoz, Jean-Louis Marty. Elsevier. 2012, (99), pp 232-237, September 15, 2012. DOI: 10.1016/j.talanta.2012.05.045.
  6. KCa3.1 and TRPM7 Channels at the Uropod Regulate Migration of Activated Human T Cells. Zerrin Kuras, Yeo-Heung Yun, Ameet A. Chimote, Lisa Neumeier, Laura Conforti. PLoS ONE 7(8), e43859. August 27, 2012. DOI: 10.1371/journal.pone.0043859.
  7. Synthesis and evaluation of cell-permeable biotinylated PU-H71 derivatives as tumor Hsp90 probes. Tony Taldone, Anna Rodina, Erica M. DaGama Gomes, Matthew Riolo, Hardik J. Patel, Raul Alonso-Sabadell, Danuta Zatorska, Maulik R. Patel, Sarah Kishinevsky and Gabriela Chiosis. Beilstein J. Org. Chem. 2013, 9 pp 544-556. March 15, 2013. DOI: 10.3762/bjoc.9.60.
  8. 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.
  9. Efficient Short Interference RNA Delivery to Tumor Cells Using a Combination of Octaarginine, GALA and Tumor-Specific, Cleavable Polyethylene Glycol System. Yu SAKURAI, Hiroto HATAKEYAMA, Hidetaka AKITA, Motoi OISHI, Yukio NAGASAKI, Shiro FUTAKI and Hideyoshi HARASHIMA. Biol. Pharm. Bull. 2009, 32 (5) pp 928-932. May 1, 2009. doi:10.1248/bpb.32.928.
  10. Development of Robust and Standardized Cantilever Sensors Based on Biotin/Neutravidin Coupling for Antibody Detection. Jiayun Zhang, Hans Peter Lang, Felice Battiston, Natalija Backmann, Francois Huber and Christoph Gerber. Sensors. 2013, 13 pp5273-5285. April 19, 2013. doi:10.3390/s130405273.
  11. Synthesis of Biotinylated r-D-Mannoside or N-Acetyl _-D-Glucosaminoside Decorated Gold Nanoparticles: Study of Their Biomolecular Recognition with Con A and WGA Lectins. Xiaoze Jiang, Abdelghani Housni, Guillaume Gody, Paul Boullanger, Marie-The´re`se Charreyre, Thierry Delair, and Ravin Narain. Bioconjugate Chem. 2010, 21 pp 521–530. February 3, 2010. DOI: 10.1021/bc900431p.
  12. An Investigation of Phosphorous-Based Bioconjugation Techniques for Protein Modification. Maja Lopandic. UWSPACE. 2022. April 7, 2022. http://hdl.handle.net/10012/18138.

Applicable patents and legal notices are available at legal notices.

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