Structure via PubChem · Public domain (PubChem)
N-hydroxysuccinimide
Sign in to saveAlso known as N -Hydroxysuccinimide，NHS
'''N-Hydroxysuccinimide (NHS''') is an organic compound with the formula (CH2CO)2NOH. It is a white solid that is used as a reagent for preparing active esters in peptide synthesis. It can be synthesized by heating succinic anhydride with hydroxylamine or hydroxylamine hydrochloride.
Chemical data
- Formula
- C4H5NO3
- Molecular weight
- 115.09 g/mol
- IUPAC name
- 1-hydroxypyrrolidine-2,5-dione
- SMILES
- C1CC(=O)N(C1=O)O
- InChIKey
- NQTADLQHYWFPDB-UHFFFAOYSA-N
- XLogP
- -1.4
- Polar surface area
- 57.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- heterocyclic compound
- Has part
- hydrogen
- Mass
- 115.027
- Image
- N-Hydroxysuccinimide powder.jpg
Show 5 more facts
- Commons category
- N-Hydroxysuccinimide
- chemical formula
- C₄H₅NO₃
- found in taxon
- Escherichia coli
- canonical SMILES
- C1CC(=O)N(C1=O)O
- melting point
- 97.0
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Activating reagent
- Use
- Alternatives
- References
'''N-Hydroxysuccinimide (NHS''') is an organic compound with the formula (CH2CO)2NOH. It is a white solid that is used as a reagent for preparing active esters in peptide synthesis. It can be synthesized by heating succinic anhydride with hydroxylamine or hydroxylamine hydrochloride.
==Activating reagent== NHS is commonly found in organic chemistry or biochemistry where it is used as an activating reagent for carboxylic acids. Activated acids (carboxylates) can react with amines to form amides for example, whereas a normal carboxylic acid would just form a salt with an amine.
Excerpted from Wikipedia’s “N-hydroxysuccinimide” article, available under the CC BY-SA 4.0 licence.