N-Ethylmaleimide
Names | |
---|---|
Preferred IUPAC name
1-Ethyl-1H-pyrrole-2,5-dione | |
Other names
Ethylmaleimide
| |
Identifiers | |
3D model (
JSmol ) |
|
Abbreviations | NEM |
112448 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard
|
100.004.449 |
EC Number |
|
405614 | |
IUPHAR/BPS |
|
KEGG | |
PubChem CID
|
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
Properties | |
C6H7NO2 | |
Molar mass | 125.12528 |
Melting point | 43 to 46 °C (109 to 115 °F; 316 to 319 K) |
Boiling point | 210 °C (410 °F; 483 K) |
Hazards | |
GHS labelling: | |
Danger | |
H300, H301, H311, H314, H317 | |
P260, P261, P264, P270, P272, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P333+P313, P361, P363, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
N-Ethylmaleimide (NEM) is an organic compound that is derived from maleic acid. It contains the amide functional group, but more importantly it is an alkene that is reactive toward thiols and is commonly used to modify cysteine residues in proteins and peptides.[2]
Organic chemistry
NEM is a Michael acceptor in the
Case studies
NEM blocks
N-Ethylmaleimide was used by
NEM activates ouabain-insensitive Cl-dependent K efflux in low K sheep and goat red blood cells.[5] This discovery contributed to the molecular identification of K-Cl cotransport (KCC) in human embryonic cells transfected by KCC1 isoform cDNA, 16 years later.[6] Since then, NEM has been widely used as a diagnostic tool to uncover or manipulate the membrane presence of K-Cl cotransport in cells of many species in the animal kingdom.[7] Despite repeated unsuccessful attempts to identify chemically the target thiol group,[8] at physiological pH, NEM may form adducts with thiols within protein kinases that phosphorylate KCC at specific serine and threonine residues primarily within the C-terminal domain of the transporter.[9] The ensuing dephosphorylation of KCC by protein phosphatases leads to activation of KCC.[10]
References
- ^ N-Ethylmaleimide at Sigma-Aldrich
- ^ Thiol reactive probes Archived 2008-01-28 at the Wayback Machine at Invitrogen
- ISBN 1-57259-153-6.
- ^ Gregory, J. D. (1955) J. Am. Chem. Soc. 77, 3922-3923
- ^ A chloride dependent K+ flux induced by N ethylmaleimide in genetically low K+ sheep and goat erythrocytes.P.K. Lauf and B.E. Theg. Biochem. Biophys. Res. Comm., 92:1422, 1980
- ^ Gillen CM, Brill S, Payne JA, Forbush B 3rd: Molecular cloning and functional expression of the K-Cl cotransporter from rabbit, rat, and human. A new member of the cation-chloride cotransporter family.J Biol Chem. 1996 Jul 5;271(27):16237-44
- ^ Regulation of K-Cl cotransport: from function to genes. N. C. Adragna, M. Di Fulvio and P.K. Lauf, J. Membrane Biology, 200:1-29, 2004
- ^ K+ Cl Cotransport: Sulfhydryl, divalent cations and the mechanism of volume activation in a red cell. P.K. Lauf. Topical Review, J. Memb. Biol. 88:1 13, 1985
- PMID 19665974.
- ^ Jennings, M. L. & Al-Rohil, N. S. J. gen. Physiol. 95, 1021−1040, 1990
External links
- The MEROPS online database for peptidases and their inhibitors: NEM[permanent dead link]
- The bifunctional analogues such as p-NN'-phenylenebismaleimide can be used as cross-linking reagent for cystine residues. see Lutter, L. C., Zeichhardt, H., Kurland, C. G. & Stoffier,G. (1972) Mol. Gen. Genet. 119, 357-366.