N-Hydroxysuccinimide: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

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| Name = ''N''-Hydroxysuccinimide

| = N-Hydroxysuccinimide.png

| ImageSizeL1 = 110px

| N-hydroxysuccinimide

| ImageFileR1 = N-Hydroxysuccinimide 3D ball.png

| ImageSizeR1 = 140

| ImageAltR1 = Ball-and-stick model of the N-hydroxysuccinimide molecule

| ImageFile2 = N-Hydroxysuccinimide powder.jpg

| ImageSize2 = 255

| PIN = 1-Hydroxypyrrolidine-2,5-dione

| OtherNames = HOSu, HSI.

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite}}

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = MJE3791M4T

| PubChem = 80170

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 72416

| SMILES = O=C1N(O)C(=O)CC1

| InChI = 1/C4H5NO3/c6-3-1-2-4(7)5(3)8/h8H,1-2H2

| InChIKey = NQTADLQHYWFPDB-UHFFFAOYAM

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C4H5NO3/c6-3-1-2-4(7)5(3)8/h8H,1-2H2

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = NQTADLQHYWFPDB-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| Appearance = Colourless solid

| Formula = C₄H₅NO₃

| MolarMass = 115./mol

| MeltingPtC = 96.3

| MeltingPt_ref=<ref>{{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = [[CRC Handbook of Chemistry and Physics]] | edition = 97th | publisher = [[CRC Press]] | isbn = 9781498754293|page=3.316}}</ref>

}}

|Section8={{Chembox Related

| = [[imide]]s

| = [[Succinimide]]<br />[[N-Bromosuccinimide|''N''-Bromosuccinimide]]

}}

'''''N''-Hydroxysuccinimide''' (NHS) is compound with a [[ ]] . [[ ]] [[]].<ref>{{cite |title=N-Hydroxysuccinimide

|author=Knight, David W.|encyclopedia=Encyclopedia of Reagents for Organic Synthesis|year=2001|doi=10.1002/047084289X.rh069|isbn=0471936235 }}</ref>

==Activating reagent==

is commonly found in organic chemistry or biochemistry where it is used as an activating reagent for [[carboxylic acid]]s. ) can react with [[amine]]s to form [[amide]]s for example, whereas a normal carboxylic acid would just form a salt with an amine.

==Use==

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 [[peptide synthesis|coupling reagent]] such as [[dicyclohexylcarbodiimide]] DCC or [[ethyl(dimethylaminopropyl)carbodiimide]] (EDC) is then added to form a highly activated acid intermediate. NHS reacts to a less labile activated acid. The group is usually written as SuO- or -OSu in chemical notation.

Such an ester with 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]] commercially available, and can be added to a protein to obtain a fluorescently labeled protein in reaction and purification step).

NHS can be used with EDC to immobilize [[Enzyme|enzymes]] for [[biosensor]] applications.<ref>{{Cite journal|last1=Camargo|first1=Jéssica Rocha|last2=Baccarin|first2=Marina|last3=Raymundo-Pereira|first3=Paulo A.|last4=Campos|first4=Anderson M.|last5=Oliveira|first5=Geiser G.|last6=Fatibello-Filho|first6=Orlando|last7=Oliveira|first7=Osvaldo N.|last8=Janegitz|first8=Bruno C.|date=2018-11-30|title=Electrochemical biosensor made with tyrosinase immobilized in a matrix of nanodiamonds and potato starch for detecting phenolic compounds|url=https://www.sciencedirect.com/science/article/pii/S0003267018307402|journal=Analytica Chimica Acta|language=en|volume=1034|pages=137–143|doi=10.1016/j.aca.2018.06.001|pmid=30193627 |s2cid=52174400 }}</ref>

==Alternatives==

Some alternatives to NHS are the water-soluble analog [[-NHS]], [[]], [[]] and pentafluorophenol.

{{reflist}}