Azido-dPEG®4-NHS ester, product number QBD-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, ruthenium-catalyzed click chemistry, and copper-free (e.g., strain-promoted) click chemistry. 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 has shown that 2,3,5,6-tetrafluorophenyl (TFP) esters are more hydrolytically stable and have better reactivity with amines than NHS esters.
| Unit Size | 100 mg, 1000 mg |
|---|---|
| Molecular Weight | 388.37; single compound |
| Chemical formula | C₁₅H₂₄N₄O₈ |
| CAS | 944251-24-5 |
| Purity | > 98% |
| Spacers | dPEG® Spacer is 16 atoms and 17.7 Å |
| Shipping | Ambient |
| Typical solubility properties (for additional information contact Customer Support) | Methylene chloride, Acetonitrile, DMAC, or DMSO. |
| 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. |
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.
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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.
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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.
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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.
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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
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