N-Hydroxysuccinimide

N-Hydroxysuccinimide (NHS) is a commonly used reagent in biochemistry and organic chemistry. It is a white, crystalline powder that is soluble in water and most organic solvents.

Chemical Structure

N-Hydroxysuccinimide has a simple chemical structure, consisting of a five-membered ring with two oxygen atoms, one nitrogen atom, and two carbon atoms. The nitrogen atom is bonded to a hydroxyl group, giving the compound its name.

File:N-Hydroxysuccinimide structure.png

Chemical structure of N-Hydroxysuccinimide

Uses

NHS is most commonly used in the synthesis of amides and esters from carboxylic acids. It is particularly useful in the synthesis of peptides, where it is used to activate the carboxyl groups of amino acids, allowing them to react with the amino groups of other amino acids to form peptide bonds.

In addition to its use in peptide synthesis, NHS is also used in the preparation of immunoconjugates, where it is used to link antibodies to other molecules, such as drugs or fluorescent dyes. This is done by reacting the NHS with the carboxyl groups on the antibodies, forming an active ester that can then react with the amine groups on the other molecule.

Safety

NHS is a relatively safe compound to handle, but it can cause irritation if it comes into contact with the skin or eyes. It can also be harmful if swallowed or inhaled. As with all chemicals, it should be handled with care and appropriate safety precautions should be taken.

See Also

• Esterification
• Peptide synthesis
• Immunoconjugate