N-ethylmaleimide
'''N-Ethylmaleimide (NEM''') is an organic compound that is derived from maleic acid. It is a unstable substance that reacts rapidly with thiols and is commonly used to modify cysteine residues in proteins and peptides.
Research
12,460 papers- N-Ethylmaleimide increases KCC2 cotransporter activity by modulating transporter phosphorylation.The Journal of biological chemistry · 2017
- NSF--fusion and beyond.Trends in cell biology · 1998
- N-ETHYLMALEIMIDE INHIBITION OF HORSESHOE CRAB HEMOCYTE AGGLUTINATION.Science (New York, N.Y.) · 1964
- N-Ethylmaleimide differentiates between the M(2)- and M(4)-autoreceptor-mediated inhibition of acetylcholine release in the mouse brain.Naunyn-Schmiedeberg's archives of pharmacology · 2018
- Nociceptive behavior induced by the endogenous opioid peptides dynorphins in uninjured mice: evidence with intrathecal N-ethylmaleimide inhibiting dynorphin degradation.International review of neurobiology · 2009
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Article
4 sectionsContents
- Organic chemistry
- Case studies
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'''N-Ethylmaleimide (NEM') is an organic compound that is derived from maleic acid. It is a unstable substance that reacts rapidly with thiols and is commonly used to modify cysteine residues in proteins and peptides.
==Organic chemistry== NEM is a Michael acceptor in the Michael reaction, which means that it adds into nucleophiles such as thiols. The resulting thioether features is a strong C–S bond and the reaction is virtually irreversible. Reaction with thiols occur in the pH range 6.5–7.5, NEM may react with amines or undergo hydrolysis at a more alkaline pH. NEM has been widely used to probe the functional role of thiol groups in enzymology. NEM is an irreversible inhibitor of all cysteine peptidases, with alkylation occurring at the active site thiol group (see schematic). thumb|center|500px|Mechanism of irreversible inhibition of a cysteine peptidase with NEM.