関: ethylmaleimide、NEM

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the 14th letter of the Roman alphabet (同)n

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nitrogenの化学記号
neodymiumの化学記号

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/10/22 19:55:35」(JST)

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N-Ethylmaleimide (NEM) is an organic compound that is derived from maleic acid. It contains the imide 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[edit]

NEM is a Michael acceptor, which means that it adds nucleophiles such as thiols. The resulting thioether features 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).^[3]^[4]

Mechanism of irreversible inhibition of a cysteine peptidase with NEM.

Case studies[edit]

NEM blocks vesicular transport. In lysis buffers, 20 to 25 mM of NEM is used to inhibit de-sumoylation of proteins for Western Blot analysis. NEM has also been used as an inhibitor of deubiquitinases.

N-Ethylmaleimide was used by Arthur Kornberg and colleagues to knock out DNA polymerase III in order to compare its activity to that of DNA polymerase I (pol III and I, respectively). Kornberg had been awarded the Nobel Prize for discovering pol I, then believed to be the mechanism of bacterial DNA replication, although in this experiment he showed that pol III was the actual replicative machinery.

References[edit]

^ N-Ethylmaleimide at Sigma-Aldrich
^ Thiol reactive probes at Invitrogen
^ Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.
^ Gregory, J. D. (1955) J. Am. Chem. Soc. 77, 3922-3923

External links[edit]

The MEROPS online database for peptidases and their inhibitors: NEM
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.

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English Journal

A new LC-MS/MS method for the clinical determination of reduced and oxidized glutathione from whole blood.

Moore T, Le A, Niemi AK, Kwan T, Cusmano-Ozog K, Enns GM, Cowan TM.SourceDepartment of Pathology, Stanford University School of Medicine, Stanford, CA 94305, United States.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.J Chromatogr B Analyt Technol Biomed Life Sci.2013 Jun 15;929C:51-55. doi: 10.1016/j.jchromb.2013.04.004. Epub 2013 Apr 12.
Reduced levels of glutathione (γ-glutamylcysteinylglycine, GSH) and the ratio of GSH to glutathione disulfide (GSSG) can serve as important indicators of oxidative stress and disease risk. Measured concentrations of GSH and GSSG vary widely between laboratories, largely due to the instability of GS
PMID 23660247

N-ethylmaleimide activates a Cl(-)-independent component of K(+) flux in mouse erythrocytes.

Shmukler BE, Hsu A, Alves J, Trudel M, Rust MB, Hubner CA, Rivera A, Alper SL.SourceDivisions of Nephrology and Molecular and Vascular Medicine, Beth Israel Deaconess Medical Center, USA.
Blood cells, molecules & diseases.Blood Cells Mol Dis.2013 Jun;51(1):9-16. doi: 10.1016/j.bcmd.2013.02.004. Epub 2013 Mar 6.
The K-Cl cotransporters (KCCs) of mouse erythrocytes exhibit higher basal activity than those of human erythrocytes, but are similarly activated by cell swelling, by hypertonic urea, and by staurosporine. However, the dramatic stimulation of human erythroid KCCs by N-ethylmaleimide (NEM) is obscured
PMID 23481459

Antinociceptive effect and gastroprotective mechanisms of 3,5-diprenyl-4-hydroxyacetophenone from Ageratina pichinchensis.

Sánchez-Mendoza ME, Rodríguez-Silverio J, Rivero-Cruz JF, Rocha-González HI, Pineda-Farías JB, Arrieta J.SourceEscuela Superior de Medicina, Instituto Politécnico Nacional, Plan de San Luis y Díaz Mirón, Colonia Santo Tomás, Delegación Miguel Hidalgo, 11340, México, D. F. Mexico. Electronic address: mesmendoza@hotmail.com.
Fitoterapia.Fitoterapia.2013 Jun;87C:11-19. doi: 10.1016/j.fitote.2013.03.015. Epub 2013 Mar 22.
The present study aimed to evaluate the antinociceptive activity (in inflammatory and neuropathic pain models) and gastroprotective effect of the 3,5-diprenyl-4-hydroxyacetophenone (HYDP), isolated from Ageratina pichinchensis. The gastroprotective activity of this plant was previously reported by o
PMID 23529015

Japanese Journal

Putative role of intracellular Zn^<2+> release during oxidative stress : a trigger to restore cellular thiol content that is decreased by oxidative stress

KINAZAKI Akio,CHEN Hongqin,KOIZUMI Kazuki,KAWANAI Takuya,OYAMA Tomohiro M.,SATOH Masaya,ISHIDA Shiro,OKANO Yoshiro,OYAMA Yasuo
The journal of physiological sciences : JPS 61(5), 403-409, 2011-09-01
NAID 10029575751

Functional analysis of the protein encoded by the virulence gene psvA of Pseudomonas syringae pv. eriobotryae

Kamiunten Hiroshi,Sakamaki Ikuko,Matsuo Mitsuhiro,上運天博,坂巻幾子,松尾光弘,カミウンテンヒロシ,サカマキイクコ,マツオミツヒロ
宮崎大学農学部研究報告 57, 1-10, 2011-02-28
… the N-terninal region (psvAN, nucleotides (nt) 1-1386), and the C-terminal region (psvAC, nt 1387-2193). … The enzymatic activity of GST-PsvAC was inhibited by the cysteine protease inhibitor N-ethylmaleimide, but not by the serine protease inhibitor phenylmethanesulfonyl fluoride. … Furthermore, an N-terminal deletion mutant of PsvAN-CAT was not detected in the outer membrane fraction. …
NAID 120003913446

「N-エチルマレイミド」

N-Ethylmaleimide
	IUPAC name 1-Ethylpyrrole-2,5-dione
	Other names Ethylmaleimide
Identifiers
Abbreviations	NEM
CAS number	128-53-0
PubChem	4362
ChemSpider	4209
UNII	O3C74ACM9V
DrugBank	DB02967
KEGG	C02441
ChEBI	CHEBI:44485
ChEMBL	CHEMBL8211
Jmol-3D images	Image 1
	SMILES O=C1\C=C/C(=O)N1CC ;
	InChI InChI=1S/C6H7NO2/c1-2-7-5(8)3-4-6(7)9/h3-4H,2H2,1H3 ; Key: HDFGOPSGAURCEO-UHFFFAOYSA-N InChI=1/C6H7NO2/c1-2-7-5(8)3-4-6(7)9/h3-4H,2H2,1H3; Key: HDFGOPSGAURCEO-UHFFFAOYAE ;
Properties
Molecular formula	C6H7NO2
Molar mass	125.12528
Melting point	43-46 °C
Boiling point	210 °C, 483 K, 410 °F
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

英: N-ethylmaleimide、NEM
関: エチルマレイミド

「NEM」

　　[★]

N-エチルマレイミド

関: N-ethylmaleimide

「soluble N-ethylmaleimide-sensitive factor attachment protein」

　　[★]

可溶性N-エチルマレイミド感受性因子付着タンパク質

関: SNAP、soluble NSF attachment protein

「N-ethylmaleimide-sensitive factor」

　　[★]

N-エチルマレイミド感受性因子

関: N-ethylmaleimide-sensitive protein、NSF

「N-ethylmaleimide-sensitive protein」

　　[★]

Nエチルマレイミド感受性タンパク質

関: N-ethylmaleimide-sensitive factor

「n」

　　[★]

n.

例数

関: number of experiment、sample size

pの前の[n]はmと記載する。synptom→symptom

「N」

　　[★]

アスパラギン asparagine
窒素(原子、分子)

「ethylmaleimide」

　　[★]

エチルマレイミド

関: N-ethylmaleimide

「Nd」

　　[★] ネオジム neodymium 　

[1] N-Ethylmaleimide at Sigma-Aldrich

[2] Thiol reactive probes at Invitrogen

[3] Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.

[4] Gregory, J. D. (1955) J. Am. Chem. Soc. 77, 3922-3923

リンク元	「N-エチルマレイミド」「NEM」
拡張検索	「soluble N-ethylmaleimide-sensitive factor attachment protein」「N-ethylmaleimide-sensitive factor」「N-ethylmaleimide-sensitive protein」
関連記事	「n」「N」「ethylmaleimide」「Nd」

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案内

案内

N-ethylmaleimide