Description

Biotin-dPEG®7-NH2 (Biotin-dPEG®7-amine), product number QBD-10826, is a short (25 atoms, 29.8 Å), hydrophilic, water-soluble, discrete PEG biotinylation product that reacts with carboxylic acids and their activated esters [N-hydroxysuccinimidyl (NHS), 2,3,5,6-tetrafluorophenyl (TFP)] to form stable amide bonds. Additionally, Biotin-dPEG®7-NH2 forms amide bonds directly with carboxylic acids using 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) chemistry. Furthermore, the product can react with carbonyl groups (aldehydes or ketones) to form a labile Schiff base, which can be reduced to a secondary amine using sodium cyanoborohydride for additional conjugate stability.

Amphiphilic biotin-dPEG®7-NH2 dissolves equally well in both aqueous buffer and organic solvent. It is not necessary to dissolve this product in an organic solvent before using it in aqueous reaction media. Furthermore, biotinylation of biomacromolecules with QBD-10826 will not cause aggregation and precipitation. Eliminating aggregation should consequently improve the signal-to-noise ratio of applications developed with this product. Aldehydes are uncommon in biomacromolecules. However, the oxidation of reducing sugars in glycosylated proteins (for example, using sodium periodate) forms aldehydes on the carbohydrate coats of glycoproteins. Reacting Biotin-dPEG®7-amine with aldehydes will produce labile imines or Schiff bases that can be reduced under mild conditions with sodium cyanoborohydride to form more stable secondary amines.

Any application that can take advantage of the strong biotin-avidin/ streptavidin affinity can use Biotin-dPEG®7-NH2. The terminal amine of QBD-10826 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®7-NH2 expands the range of molecules and nanoparticles for which dPEG®-biotin is useful.

Specifications

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. 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.

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.

Protein Microarray Immobilization via Epoxide Ring-Opening by Thiol, Amine, and Azide. Seyed Mohammad Mahdi Dadfar, Sylwia Sekula-Neuner, Vanessa Trouillet, Michael Hirtz. Advanced Materials Interfaces. 2021. Volume 8, Issue 10. March 18, 2021. https://doi.org/10.1002/admi.202002117

Description

Biotin-dPEG®23-NH2 (Biotin-dPEG®23-amine), product number QBD-10786, is a carboxylate-reactive biotinylation product on a long (71 atoms), single molecular weight, discrete PEG (dPEG®) spacer. Biotin-dPEG®23-NH2 reacts with activated esters (N-hydroxysuccinimide, 2,3,5,6-tetrafluorophenyl) of carboxylic acids under slightly basic conditions. Moreover, it can be coupled directly to a carboxylic acid using 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) chemistry. Additionally, the product reacts with aldehydes or ketones to form a labile Schiff base. The Schiff base can be reduced to a secondary amine using sodium cyanoborohydride if additional conjugate stability is necessary.
Amphiphilic Biotin-dPEG®23-NH2 dissolves equally well in both aqueous media and organic solvents. Therefore, it is unnecessary to dissolve this product in an organic solvent before using it in an aqueous reaction. Furthermore, biotinylation of biomacromolecules with Biotin-dPEG®23-NH2 will not cause aggregation and precipitation. Eliminating aggregation and precipitation improves the signal-to-noise ratio of applications developed with this product. Reactions with carboxylic acids or active esters of carboxylic acids yield stable amide bonds. Aldehydes are not commonly found in biomacromolecules but can be formed by oxidizing reducing sugars in glycosylated proteins. Reactions with aldehydes create labile imines (Schiff bases) that can be reduced under mild conditions with sodium cyanoborohydride to form more stable secondary amines.

Biotin-dPEG®23-NH2 works in any application that can take advantage of the exceptionally strong biotin-avidin/streptavidin affinity. The terminal amine of QBD-10786 offers the opportunity (1) to biotinylate the carbohydrate coat of glycoproteins by oxidizing reducing sugars to aldehydes and (2) to biotinylate surfaces consisting of carboxylic acids or their active esters. Thus, this product expands the range of molecules and nanoparticles in which dPEG®-biotin can be employed.

Specifications

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. 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.

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.

Blood Plasma-Derived Anti-Glycan Antibodies to Sialylated and Sulfated Glycans Identify Ovarian Cancer Patients. Tatiana Pochechueva, Alexander Chinarev, Andreas Schoetzau, Andre Fedier, Nicolai V. Bovin, Neville F. Hacker, Francis Jacob, Viola Heinzelmann-Schwarz. Plos One. 2016, 11 (10) e0164230. October 20, 2016. DOI: 10.1371/journal.pone.0164230.

Poly(catecholamine) coating and biofunctionalization of CsPbBr3 microcrystals. Sangyeon Cho and Seok Hyun Yun. ChemRxiv. 2021. License: CC BY-NC-ND 4.0. DOI: 10.26434/chemrxiv.14049710.v2

Description

Biotin-dPEG®11-NH2 (Biotin-dPEG®11-amine), product number QBD-10196, is a medium-length, hydrophilic, water-soluble, discrete PEG biotinylation product that reacts with carbonyls, carboxylic acids, and the activated esters (N-hydroxysuccinimide, 2,3,5,6-tetrafluorophenyl) of carboxylic acids. Additionally, Biotin-dPEG®11-NH2 couples directly to a carboxylic acid using 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) chemistry. Furthermore, the product can react with carbonyl groups (aldehydes or ketones) to form a Schiff base, which can be reduced to a secondary amine using sodium cyanoborohydride if additional conjugate stability is necessary.

Amphiphilic biotin-dPEG®11-NH2 dissolves equally well in both aqueous buffer and organic solvent. It is not necessary to dissolve this product in an organic solvent before using it in aqueous reaction media. Furthermore, biotinylation of biomacromolecules with QBD-10196 will not cause aggregation and precipitation. Eliminating aggregation should consequently improve the signal-to-noise ratio of 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. However, the oxidation of reducing sugars in glycosylated proteins forms aldehydes in glycosylated proteins. Reactions with aldehydes will produce labile imines or Schiff bases that can be reduced under mild conditions with sodium cyanoborohydride to form more stable secondary amines.

Any application that can take advantage of the strong biotin-avidin/ streptavidin affinity can use Biotin-dPEG®11-NH2. The terminal amine of QBD-10196 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®11-NH2 expands the range of molecules and nanoparticles for which dPEG®-biotin is useful.

Specifications

Documents

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. Compact Biocompatible Quantum Dots via RAFT-Mediated Synthesis of Imidazole-Based Random Copolymer Ligand. Wenhao Liu, Andrew B. Greytak, Jungmin Lee, Cliff R. Wong, Jongnam Park, Lisa F. Marshall, Wen Jiang, Peter N. Curtin, Alice Y. Ting, Daniel G. Nocera, Dai Fukumura, Rakesh K. Jain and Moungi G. Bawendi. J. Am. Chem. Soc. 2010, 132 (2) pp 472–483. December 21, 2009. DOI: 10.1021/ja908137d.

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

Documents

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.