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I1149

Sigma-Aldrich

Yodoacetamida

BioUltra

Sinónimos:

2-Iodoacetamide, Monoiodoacetamide, alpha-Iodoacetamide

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About This Item

Fórmula lineal:
ICH2CONH2
Número de CAS:
144-48-9
Peso molecular:
184.96
Beilstein/REAXYS Number:
1739080
EC Number:
205-630-1
MDL number:
MFCD00008028
UNSPSC Code:
12352202
PubChem Substance ID:
24278486
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

300

product line

BioUltra

assay

≥99% (NMR)

form

powder

impurities

≤0.0005% Phosphorus (P)
≤0.1% Insoluble matter

mp

92-95 °C (lit.)

solubility

H2O: 0.5 M, clear, colorless

anion traces

chloride (Cl-): ≤0.05%
sulfate (SO42-): ≤0.05%

cation traces

Al: ≤0.0005%
Ca: ≤0.0005%
Cu: ≤0.0005%
Fe: ≤0.0005%
K: ≤0.005%
Mg: ≤0.0005%
NH4+: ≤0.05%
Na: ≤0.05%
Pb: ≤0.001%
Zn: ≤0.0005%

storage temp.

2-8°C

SMILES string

NC(=O)CI

InChI

1S/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5)

InChI key

PGLTVOMIXTUURA-UHFFFAOYSA-N

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Application

Iodoacetamide has been used:
  • in protein digestion for proteomic analysis
  • to alkylate protein samples
  • in the denaturation of cow′s milk allergens, β-lactoglobulin (BLG) and α-lactalbumin (ALA)

Biochem/physiol Actions

Iodoacetamide (IAA) is used to inhibit glycolysis due to its ability to irreversibly inhibit the glycolytic enzyme glyceraldehyde-3-phosphate dehydrogenase (GAPDH). IAA is used to investigate the role of cysteine residues in enzyme catalysis and the brain cell transport process. It can react with low molecular weight thiol compounds like mercaptoethanol and glutathione. IAN may also block enzymes like bromelain, cathepsin C, clostripain, and carboxypeptidase P.
La yodoacetamida actúa como alquilante de los restos de cisteína en la secuenciación peptídica. Es un inhibidor irreversible de enzimas que tienen cisteína en el sitio activo. Reacciona mucho más despacio con los restos de histidina, pero esta actividad es responsable de la inhibición de las ribonucleasas.

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pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 4 - Resp. Sens. 1 - Skin Sens. 1

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificados de análisis (COA)

Lot/Batch Number
0000409416
0000409416
0000409427
0000394671
0000394663

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Mirko Zaffagnini et al.
Antioxidants & redox signaling, 16(1), 17-32 (2011-06-29)
Cysteines (Cys) made acidic by the protein environment are generally sensitive to pro-oxidant molecules. Glutathionylation is a post-translational modification that can occur by spontaneous reaction of reduced glutathione (GSH) with oxidized Cys as sulfenic acids (-SOH). The reverse reaction (deglutathionylation)
Tommy Weiss-Sadan et al.
Theranostics, 9(20), 5731-5738 (2019-09-20)
Despite the common use of lipid-lowering medications, cardiovascular diseases continue to be a significant health concern. Atherosclerosis, one of the most frequent causes of cardiovascular morbidity, involves extensive inflammatory activity and remodeling of the vascular endothelium. This relentless inflammatory condition
Konstantinos Boulias et al.
Molecular cell, 75(3), 631-643 (2019-07-08)
mRNAs are regulated by nucleotide modifications that influence their cellular fate. Two of the most abundant modified nucleotides are N6-methyladenosine (m6A), found within mRNAs, and N6,2'-O-dimethyladenosine (m6Am), which is found at the first transcribed nucleotide. Distinguishing these modifications in mapping
Valentina R Minciacchi et al.
Oncotarget, 6(13), 11327-11341 (2015-04-11)
Large oncosomes (LO) are atypically large (1-10 µm diameter) cancer-derived extracellular vesicles (EVs), originating from the shedding of membrane blebs and associated with advanced disease. We report that 25% of the proteins, identified by a quantitative proteomics analysis, are differentially
Elena B Lugli et al.
Arthritis research & therapy, 17, 9-9 (2015-01-21)
Smoking is a well-established risk factor for rheumatoid arthritis (RA), and it has been proposed that smoking-induced citrullination renders autoantigens immunogenic. To investigate this mechanism, we examined human lung tissue from 40 subjects with defined smoking status, with or without
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