Azido-dPEG®₁₂-acid

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Azido-dPEG®12-acid, product number 10513, is a crosslinking reagent designed primarily for click chemistry. The azide moiety reacts in copper(I)-catalyzed, ruthenium-catalyzed, and strain promoted azide-alkyne cycloadditions (CuAAC, RuAAC, and SPAAC, respectively). Alternatively, the azide functions as a masked amine. In this role, the carboxylic acid end of the molecule must couple with an amine to form an amide bond. The azide group is then reduced to a primary amine to permit crosslinking with a carboxylic acid group. A water-soluble, single molecular weight, discrete polyethylene glycol (dPEG®) spacer separates the azide and propionic acid groups. The propanoic acid moiety can be coupled to a primary or secondary amine by an acylation reaction.

Traditional PEGylation Reagents and dPEG® Products

PEGylation is the process of modifying biomolecules and surfaces with polyethylene glycol (PEG). Traditionally, PEG products are non-uniform, disperse polymers comprised of multiple, different chain lengths of PEG, with each chain having a different molecular weight. The stated sizes of conventional PEG products are averages of the various chain lengths and molecular weights of PEG in the polymer mixture.

Quanta BioDesign’s products consist of discrete chain lengths of PEG. With only one chain length, the product has a single molecular weight. Thus, we name our PEG products “discrete PEG” products, and we sell them under the dPEG® tradename.

For more information on Quanta BioDesign’s dPEG® technology, please visit our “What is dPEG®?” page. For answers to our most frequently asked questions, please click here.

Click Chemistry and dPEG® Products

From the first report by K. Barry Sharpless and colleagues 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). Classical CuAAC chemistry forms a 1,4-disubstituted triazole ring. Ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) operates similarly to CuAAC but gives rise to 1,5-disubstituted triazole rings. Later, 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. {link}

The Carboxylic Acid Group of Azido-dPEG®12-acid

The carboxylic acid group of Azido-dPEG®12-acid can be coupled directly to a free amine using EDC or some other carbodiimide. Also, forming the active ester of the acid using N-hydroxysuccinimide (NHS) or 2,3,5,6-tetrafluorophenol (TFP) before reacting with free amines is a useful course of action.

Commercial Scale Production Is Available for Azido-dPEG®12-acid

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.

Related Products

This product is one of several azido-dPEG®-acid products with varying lengths of dPEG® spacers. Quanta BioDesign also offers a complete line of click chemistry products. The list of these products is here.

Act Now

Stop using conventional click chemistry crosslinkers! You can do better. Our click chemistry crosslinking reagents offer water solubility, improved hydrodynamic volume, no background noise (which means better signal), and no protein precipitation caused by aggregation. Why would you not use something better?

For cleaner click chemistry crosslinking, click the “Add to Cart” button now. You will not regret it. Click “Add to Cart” now.

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.

Description

Azido-dPEG®12-acid, product number 10513, is a crosslinking reagent designed primarily for click chemistry. The azide moiety reacts in copper(I)-catalyzed, ruthenium-catalyzed, and strain promoted azide-alkyne cycloadditions (CuAAC, RuAAC, and SPAAC, respectively). Alternatively, the azide functions as a masked amine. In this role, the carboxylic acid end of the molecule must couple with an amine to form an amide bond. The azide group is then reduced to a primary amine to permit crosslinking with a carboxylic acid group. A water-soluble, single molecular weight, discrete polyethylene glycol (dPEG®) spacer that is 40 atoms (46.4 Å) long separates the azide and propionic acid groups. The propanoic acid moiety can be coupled to a primary or secondary amine by an acylation reaction.

Traditional PEGylation Reagents and dPEG® Products

PEGylation is the process of modifying biomolecules and surfaces with polyethylene glycol (PEG). Traditionally, PEG products are non-uniform, disperse polymers comprised of multiple, different chain lengths of PEG, with each chain having a different molecular weight. The stated sizes of conventional PEG products are averages of the various chain lengths and molecular weights of PEG in the polymer mixture.

Quanta BioDesign’s products consist of discrete chain lengths of PEG. With only one chain length, the product has a single molecular weight. Thus, we name our PEG products “discrete PEG” products, and we sell them under the dPEG® tradename.

For more information on Quanta BioDesign’s dPEG® technology, please visit our “What is dPEG®?” page. For answers to our most frequently asked questions, please click here.

Click Chemistry and dPEG® Products

From the first report by K. Barry Sharpless and colleagues 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). Classical CuAAC chemistry forms a 1,4-disubstituted triazole ring. Ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) operates similarly to CuAAC but gives rise to 1,5-disubstituted triazole rings. Later, 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.

The Carboxylic Acid Group of Azido-dPEG®12-acid

The carboxylic acid group of Azido-dPEG®12-acid can be coupled directly to a free amine using EDC or some other carbodiimide. Also, forming the active ester of the acid using N-hydroxysuccinimide (NHS) or 2,3,5,6-tetrafluorophenol (TFP) before reacting with free amines is a useful course of action.

Commercial Scale Production Is Available for Azido-dPEG®12-acid

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.

Related Products

This product is one of several azido-dPEG®-acid products with varying lengths of dPEG® spacers. Quanta BioDesign also offers a complete line of click chemistry products. The list of these products is here.

Act Now

Stop using conventional click chemistry crosslinkers! You can do better. Our click chemistry crosslinking reagents offer water solubility, improved hydrodynamic volume, no background noise (which means better signal), and no protein precipitation caused by aggregation. Why would you not use something better?

For cleaner click chemistry crosslinking, click the “Add to Cart” button now. You will not regret it.

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.

Additional information

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