Azido-dPEG®₁₂-NHS ester

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.

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.

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