Specs:

 SDS

Molecular Weight: 388.37; single compound

CAS: 944251-24-5

Purity: > 98%

Spacers: dPEG® Spacer is 16 atoms and 17.7 Å

Shipping: Ambient

References: 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.

Chemoselective Immobilization of Peptides on Abiotic and Cell Surfaces at Controlled Densities. Venkata R. Krishnamurthy, John T. Wilson, Wanxing Cui, XueZheng Song, Yi Lasanajak, Richard D. Cummings, and Elliot L. Chaikof. Langmuir. 2010, 26 (11) pp 7675-7678. May 7, 2010. DOI: 10.1021/la101192v.

Constant-speed vibrational signaling along polyethylene glycol chain up to 60-Å distance. Zhiwei Lin and Igor V. Rubtsov. PNAS. 2012, 109 (5) pp 1413-1418. January 31, 2012. DOI:10.1073/pnas.1116289109.

Ballistic energy transport along PEG chains: distance dependence of the transport efficiency. Zhiwei Lin , Nan Zhang , Janarthanan Jayawickramarajah and Igor V. Rubtsov. Physical Chemistry Chemical Physics. 2012, 30 (14) pp 10445-10454. April 12, 2012. DOI: 10.1039/C2CP40187H.

An Intein-Mediated Site-Specific Click Conjugation Strategy for Improved Tumor Targeting of Nanoparticle Systems. Drew R. Elias, Dr. Zhiliang Cheng, and Prof. Andrew Tsourkas. Small. 2010, 6 (21) pp 2460–2468 November 5, 2010. DOI:10.1002/smll.201001095.

Peptide-Targeted Nanoglobular Gd-DOTA Monoamide Conjugates for Magnetic Resonance Cancer Molecular Imaging. Mingqian Tan, Xueming Wu, Eun-Kee Jeong, Qianjin Chen, and Zheng-Rong Lu. Biomacromolecules. 2010, 11 (3) pp 754–761. March 8, 2010. DOI:10.1021/bm901352v.

Protein addressing on patterned microchip by coupling chitosan electrodeposition and ‘electro-click’ chemistry. Xiao-Wen Shi,, Ling Qiu, Zhen Nie, Ling Xiao, Gregory F Payne and Yumin Du. Biofabrication. 2013, (5) 041001 pp 7. September 23, 2013. DOI:10.1088/1758-5082/5/4/041001.

Clickable Poly(ethylene glycol)-Microsphere-Based Cell Scaffolds. Peter K. Nguyen, Christopher G Snyder, Jason D. Shields, Amanda W. Smith, Donald L. Elbert. Macromolecular Journals. 2013, 214 (8) pp 948-956. March 4, 2013. DOI: 10.1002/macp.201300023.

Nano-Scale Alignment of Proteins on a Flexible DNA Backbone. Tatsuya Nojima1, Hiroki Konno, Noriyuki Kodera, Kohji Seio, Hideki Taguchi, Masasuke Yoshida. PLoS ONE. 2012, 7(12): e52534. December 26, 2012. DOI:10.1371/journal.pone.0052534.

A Mild and Reliable Method to Label Enveloped Virus with Quantum Dots by Copper-Free Click Chemistry. Jian Hao, Li-Li Huang, Rui Zhang, Han-Zhong Wang and Hai-Yan Xie. Analytical Chemistry. 2012, 84 (19) pp 8364−8370. September 4, 2012. DOI: org/10.1021/ac301918t.

ADIBO-Based ”Click” Chemistry for Diagnostic Peptide Micro-Array Fabrication: Physicochemical and Assay Characteristics. Denis Prim, Fabien Rebeaud, Vincent Cosandey, Roger Marti, Philippe Passeraub and Marc E. Pfeifer. ADIBO-Based ”Click” Chemistry for Diagnostic Peptide Micro-Array Fabrication: Physicochemical and Assay Characteristics. Denis Prim, Fabien Rebeaud, Vincent Cosandey, Roger Marti, Philippe Passeraub and Marc E. Pfeifer. Molecules. 2013, 18 pp 9833-9849. August 16, 2013. DOI: 10.3390/molecules18089833.

Bio-Inspired Liposomal Thrombomodulin Conjugate through Bio-Orthogonal Chemistry. Hailong Zhang, Jacob Weingart, Rui Jiang, Jianhao Peng, Qingyu Wu, and Xue-Long Sun. Bioconjugate Chemistry. 2013, 24 (4) pp 550–559. March 4, 2013. DOI: 10.1021/bc300399f.

Design and synthesis of glycoprotein-based multivalent glyco-ligands for influenza hemagglutinin and human galectin-3. Helen Wanga, Wei Huang, Jared Orwenyo, Aditi Banerjee, Gerardo R. Vasta, Lai-Xi Wang. Bioorganic & Medicinal Chemistry. 2013, 21 (7) pp 2037–2044. April 1, 2013. DOI: 10.1016/j.bmc.2013.01.028.

A Method for Determining Small Anharmonicity Values from 2DIR Spectra Using Thermally Induced Shifts of Frequencies of High-Frequency Modes. Zhiwei Lin , Patrick Keiffer , and Igor V. Rubtsov. Journal of Physical ChemistryB. 2011, 115 (18) pp 5347-5353. December 28, 2010. DOI: 10.1021/jp1094189.

3D Tumor tissue analogs and their orthotopic implants for understanding tumor-targeting of microenvironment-responsive nanosized chemotherapy and raditation. Pallavi Sethi, PhD., Amar Jyoti, PhD, Elden P. Swindell, PhD, Ryan Chan, PharmD, Ulrich W. Langner, DABR, PhD, Jonathan M. Feddock, MD, Radhakrishnan Nagarajan, PhD, Thomas V. O'Halloran, PhD, Meenakshi Upreti, PhD. Nanomedicine. 2015, 11 (8) pp 2013-2023. July 22,2015. DOI: 10.1016/j.nano.2015.07.013.

Click Chemistry Applied to the Synthesis of Salmonella Typhimurium O-Antigen Glycoconjugate Vaccine on Solid Phase with Sugar Recycling. Giuseppe Stefanetti, Allan Saul, Calman A. MacLennan and Francesca Micoli. Bioconjugate Chemistry. 2015. November 9, 2015. DOI: 10.1021/acs.bioconjchem.5b00521.

Energy Transport in PEG Oligomers: Contributions of Different Optical Bands. Layla N Qasim, Arkady A Kurnosov, Yuankai Yue, Zhiwei Lin, Alexander L Burin, and Igor V Rubtsov. The Journal of Physical Chemistry. 2016, October 31, 2016. DOI: 10.1021/acs.jpcc.6b09389.

Streptavidin-hydrogel prepared by sortase A-assisted click chemistry for enzyme immobilization on an electrode. Takuya Matsumoto, Yuki Isogawa, Tsutomu Tanaka, and Akihiko Kondo. Biosensors and Bioelectronics. 2017, 99 (2018) pp 56-61. July 17, 2017. DOI: http://dx.doi.org/10.1016/j.bios.2017.07.044.

Lysosomal Targeting Enhancement by Conjugation of Glycopeptides Containing Mannose-6-phosphate Glycans Derived from Glyco-engineered Yeast. Ji-Yeon Kang, Keun Koo Shin, Ha Hyung Kim, Jeong-Ki Min, Eun Sun Ji, Jin Young Kim, Ohsuk Kwon, & Doo-Byoung Oh. Scientific Reports. 2018, 8 (8730) pp 1-14. June 7, 2018. DOI: 10.1038/s41598-018-26913-4.

Streptavidin-hydrogel prepared by sortase A-assisted click chemistry for enzyme immobilization on an electrode. Takuya Matsumoto, Yuki Isogawa, Tsutomu Tanaka, and Akihiko Kondo. Biosensors and Bioelectronics. 2018, 99 pp 56-61. 1/15/2018. DOI: 10.1016/j.bios.2017.07.044.

Antibody Targeted PET Imaging of 64Cu-DOTA-Anti-CEA PEGylated Lipid Nanodiscs in CEA Positive Tumors. Patty Wong, Lin Li, Junie Chea, Weidong Hu, Erasmus Poku, Todd Ebner, Nicole Bowles, Jeffrey Y. C. Wong, Paul J. Yazaki, Stephen Sligar, John E. Shively. Bioconjugate Chem. 2020, 31, 3, 743-753 January 21, 2020 DOI: https://doi.org/10.1021/acs.bioconjchem.9b00854

Click chemistry compared to thiol chemistry for the synthesis of site-selective glycoconjugate vaccines using CRM197 as carrier protein. G. Stefanetti, M. Allan, A. Usera, F. Micoli. Glycoconjugate Journal (2020). June 13, 2020. DOI: 10.1007/s10719-020-09930-2

NIR Photodynamic Destruction of PDAC and HNSCC Nodules Using Triple-Receptor-Targeted Photoimmuno-Nanoconjugates: Targeting Heterogeneity in Cancer. Bano, S.; Obaid, G.; Swain, J.W.R.; Yamada, M.; Pogue, B.W.; Wang, K.; Hasan, T.. J. Clin. Med. 2020, 9, 2390 https://doi.org/10.3390/jcm9082390

Photodynamic priming with triple-receptor targeted nanoconjugates that trigger T cell-mediated immune responses in a 3D in vitro heterocellular model of pancreatic cancer, Pushpamali De Silva ORCID, Shazia Bano ORCID, Brian W. Pogue, Kenneth K. Wang, Edward V. Maytin and Tayyaba Hasan, Nanophotonics, 2021, Volume 10 Issue 12, DOI: 10.1515/nanoph-2021-0304


Additional Search Phrases:

Azido-dPEG4-NHS ester, Azido-N-Hydroxysuccinimide, NHS-Azide, 944251245, PEG, dPEG, discrete PEG, polyethylene glycol, PEGylation reagent, azide, azide ion, azido, azido group, click chemistry, click reagent, Huisgen cycloaddition, alcohol, hydroxy, PEG spacer, amine reactive, peptide formation, crosslinker, cross linker, crosslinking, crosslinking reagent, active ester, NHS ester, N-hydroxysuccinimide, Azido-PEG4-NHS ester, N3-PEG4-NHS, NHS-PEG4-azide, Azido-PEG-NHS ester



 SDS    Datasheet

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Azido-dPEG®₄-NHS ester

$175.00 – $500.00

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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#: 10501 Categories: ,

TFP_Esters_Art2

 

Azido-dPEG®4-NHS ester, product number 10501, contains an azide group linked to an N-hydroxysuccinimidyl (NHS) ester through a single molecular weight, discrete polyethylene glycol (dPEG®) spacer. This product works with copper(I)-catalyzed or ruthenium-catalyzed click chemistry and with copper free click chemistry using Quanta BioDesign’s line of DBCO-functionalized dPEG® products. The dPEG® spacer imparts water solubility and adds hydrodynamic volume to the conjugated product. The single molecular weight product design, with its discrete chain length, simplifies analysis of this product.

NHS esters are the most popular, most widely used way to conjugate carboxylic acids to primary or secondary amines resulting in stable amide bonds. NHS esters react quickly and efficiently in aqueous media at physiological pH values (7.0 – 7.5). However, they are prone to hydrolysis over time. Moreover, the rate of hydrolysis is pH dependent. Consequently, they must be used immediately upon dissolution in water or aqueous buffer. Published research as well as work done internally by Quanta BioDesign has shown that 2,3,5,6-tetrafluorophenyl (TFP) esters are more hydrolytically stable and have better reactivity than NHS esters. For more information, please click TFP Esters Have More Hydrolytic Stability and Greater Reactivity Than NHS Esters.

  1. Barry Sharpless and colleagues defined the rapid, chemoselective, stereospecific reactions between an azide and an alkyne leading to the formation of a triazole ring as click chemistry. From its publication in 2001, click chemistry has grown consistently in popularity and importance for the development of new chemical structures. The first-reported click chemistry reactions were catalyzed by copper(I) and are known as Cu(I)-catalyzed azide alkyne cycloaddition (CuAAC). Subsequently, copper free click chemistry (formally known as strain promoted azide alkyne cycloaddition, or SPAAC) was developed by Carolyn Bertozzi and colleagues to facilitate click chemistry reactions in living cells without the use of toxic copper salts. For more information, please see Click Chemistry with dPEG® Reagents.

Quanta BioDesign offers numerous click chemistry reagents for copper(I)-catalyzed and strain-promoted click chemistry. Click here to see all of our click chemistry products.

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.

Application References:

  1. Hermanson, G. T. Chapter 3, The Reactions of Bioconjugation. Bioconjugate Techniques, 3rd edition. Academic Press: New York, 2013, pp 229-258, especially pages 233-234 (NHS esters) and pages 238-239 (fluorophenyl esters). Click here now for a review of Greg’s book and a link to purchase it.
  2. Hermanson, G. T. Chapter 17, Chemoselective Ligation; Bioorthogonal Reagents. Bioconjugate Techniques, 3rd edition. Academic Press: New York, 2013, pp 757-786, particularly pages 769-775 where click chemistry is discussed.
  3. Hermanson, G. T. Chapter 18, PEGylation and Synthetic Polymer Modification. Bioconjugate Techniques, 3rd edition. Academic Press: New York, 2013, pp 787-838.
  4. 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. https://doi.org/10.1002/1521-3773(20010601)40:11%3C2004::AID-ANIE2004%3E3.0.CO;2-5
  5. Kolb, H. C.; Sharpless, K. B. The growing impact of click chemistry on drug discovery. Drug Disc. Today, 2003, 8(24), 1128-1137. https://doi.org/10.1016/S1359-6446(03)02933-7.
  6. Baskin, J. M.; Bertozzi, C. R. Bioorthogonal Click Chemistry: Covalent Labeling in Living Systems. QSAR & Combinatorial Science 2007, 26(11–12), 1211–1219. https://doi.org/10.1002/qsar.200740086.
  7. Patterson, D. M.; Nazarova, L. A.; Prescher, J. A. Finding the Right (Bioorthogonal) Chemistry. ACS Chem. Biol. 2014, 9(3), 592–605. https://doi.org/10.1021/cb400828a.
  8. Dommerholt, J.; Rutjes, F. P. J. T.; van Delft, F. L. Strain-Promoted 1,3-Dipolar Cycloaddition of Cycloalkynes and Organic Azides. Top. Curr. Chem. (Z) 2016, 374(2), 16. https://doi.org/10.1007/s41061-016-0016-4.
  9. Johansson, J. R.; Beke-Somfai, T.; Said Stålsmeden, A.; Kann, N. Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications. Chem. Rev. 2016, 116(23), 14726–14768. https://doi.org/10.1021/acs.chemrev.6b00466.

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Additional information

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

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