Specs:

 SDS

Molecular Weight: 740.79; single compound

CAS: 1108750-59-9

Purity: > 98%

Spacers: dPEG® Spacer is 40 atoms and 47.2 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, 5 (109), 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.

Shape-Encoded Chitosan-Polyacrylamide Hybrid Hydrogel Microparticles with Controlled Macroporous Structures via Replica Molding for Programmable Biomacromolecular Conjugation. Eunae Kang, Sukwon Jung, John H. Abel, Allison Pine, and Hyunmin Yi. Langmuir. 2016, 32 (21) pp 5394-5402. May 18, 2016. DOI: 10.1021/acs.langmuir.5b04653.

Towards personalized peptide-based cancer nanovaccines: a facile and versatile synthetic approach. Hamilton Kakwere, Elizabeth S Ingham, Riley Allen, Lisa M Mahakian, Sarah M Tam, Hua Zhang, Matthew Thomas Silvestrini, Jamal S Lewis, and Katherine W. Ferrara. Bioconjugate Chemistry. 2017, pp 1-27. September 28, 2017. DOI: 10.1021/acs.bioconjchem.7b00502.




Additional Search Phrases:

Azido-dPEG12-NHS ester, Azido-N-Hydroxysuccinimide, NHS-Azide, 1108750599, 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-PEG12-NHS ester, N3-PEG12-NHS, NHS-PEG12-azide, Azido-PEG600-NHS ester, Azido-PEG-NHS ester



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Azido-dPEG®₁₂-NHS ester

$236.00 – $788.00

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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 [email protected] for Bulk Pricing and Custom Syntheses
Product#: 10505 Categories: ,

TFP_Esters_Art2

Azido-dPEG®12-NHS ester, product number 10505, 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 the 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.

From its publication in 2001 by K. Barry Sharpless and colleagues, 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, including a broad array of azide-functionalized dPEG® products and dPEG® products functionalized with dibenzyl cyclooctyne (DBCO) for SPAAC. Click here to see a complete list 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). Want to learn more about Greg’s book? 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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