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04259

Sigma-Aldrich

N-Ethylmaleimide

BioUltra, ≥99.0% (HPLC)

Synonym(s):

NEM

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About This Item

Empirical Formula (Hill Notation):
C6H7NO2
CAS Number:
128-53-0
Molecular Weight:
125.13
Beilstein/REAXYS Number:
112448
EC Number:
204-892-4
MDL number:
MFCD00005509
UNSPSC Code:
12352106
PubChem Substance ID:
329747899
NACRES:
NA.26

product line

BioUltra

Quality Level

200

assay

≥99.0% (HPLC)

impurities

insoluble matter, passes filter test

ign. residue

≤0.05%

bp

210 °C (lit.)

mp

43-46 °C (lit.)
44-47 °C

solubility

methanol: 1 M at 20 °C, clear, colorless

anion traces

chloride (Cl-): ≤50 mg/kg
sulfate (SO42-): ≤100 mg/kg

cation traces

Al: ≤5 mg/kg
Ba: ≤5 mg/kg
Bi: ≤5 mg/kg
Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤50 mg/kg
Li: ≤5 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Mo: ≤5 mg/kg
Na: ≤50 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Sr: ≤5 mg/kg
Zn: ≤5 mg/kg

absorption

cut-off at 382 nm in methanol at 1 M

storage temp.

2-8°C

SMILES string

CCN1C(=O)C=CC1=O

InChI

1S/C6H7NO2/c1-2-7-5(8)3-4-6(7)9/h3-4H,2H2,1H3

InChI key

HDFGOPSGAURCEO-UHFFFAOYSA-N

Gene Information

human ... SLC6A3(6531) , SLC6A4(6532)

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Application

N-Ethylmaleimide (NEM) has been used:
  • to prepare NEM-modified myosin beads
  • to block unmodified free thiols in samples
  • as a supplement in IP lysis/wash buffer for in vitro SUMOylation assay

Reagent for the covalent modification of cysteine residues in proteins.

Biochem/physiol Actions

Augments currents from native M-channels in sympathetic neurons and acts as an opener for KCNQ2, KCNQ4 and KCNQ5 channels.
Sulfhydryl alkylating agent that inactivates NADP-dependent isocitrate dehydrogenase and many endonucleases.

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

163.2 °F - closed cup

flash_point_c

72.9 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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SUMOylation of periplakin is critical for efficient reorganization of keratin filament network
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Molecular Biology of the Cell, 30(3), 357-369 (2019)
Measuring the kinetic and mechanical properties of non-processive myosins using optical tweezers
Greenberg MJ, et al.
Methods in Molecular Biology, 483-509 (2017)
Resin-assisted enrichment of thiols as a general strategy for proteomic profiling of cysteine-based reversible modifications
Jia Guo
Nature Protocols, 9(1), 64-75 (2014)
Koichi Tan-No et al.
International review of neurobiology, 85, 191-205 (2009-07-18)
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Nature, 488(7413), 665-669 (2012-08-17)
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