N-Hydroxysuccinimide

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N-hydroxysuccinimide
N-hydroxysuccinimide
IUPAC name 1-Hydroxy-2,5-pyrrolidinedione
Other names 1-hydroxypyrrolidine-2,5-dione
Identifiers
CAS number [6066-82-6]
Properties
Molecular formula C4H5NO3
Molar mass 115.09g/mol
Related compounds
Related imides Succinimide
N-Bromosuccinimide
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references
For other uses, see NHS (disambiguation).

N-Hydroxysuccinimide (NHS) is a compound with a molecular weight of 115.09 and a melting point of 95 °C.[1]

As it is slightly acidic, it is an irritant to skin, eyes and mucous membranes.

It is commonly found in organic chemistry or biochemistry where it is used as an activating reagent for carboxylic acids. Activated acids (basically esters with a good leaving group) can react with amines to form amides for example, whereas a normal carboxylic acid would just form a salt with an amine.

A common way to synthesize an NHS-activated acid is to mix NHS with the desired carboxylic acid and a small amount of an organic base in an anhydrous solvent. A dehydrating agent such as dicyclohexylcarbodiimide DCC or ethyl(dimethylaminopropyl) carbodiimide (EDC) is then added to form a highly unstable activated acid intermediate. NHS reacts to form a less labile activated acid. The group itself is usually written as SuO- or -OSu in chemical notation. Such an ester with an acid and NHS, sometimes called succinate ester, is stable enough to be purified and stored at low temperatures in the absence of water and, as such, is commercially available. NHS esters are commonly used for protein modification (e.g. an NHS ester of fluorescein, are commercially available, and can be added to a protein to obtain a fluorescently labeled protein in one simple reaction and purification step).

Some alternatives to NHS are the water-soluble analog Sulfo-NHS, HOBt, HOAt and pentafluorophenol.

[edit] References

  1. ^ N-Hydroxysuccinimide. Sigma-Aldrich. Retrieved on 2007-07-03.
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