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I1149

Iodoacetamide

BioUltra

Synonym(s):

2-Iodoacetamide, Monoiodoacetamide, alpha-Iodoacetamide

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About This Item

Linear Formula:
ICH2CONH2
CAS Number:
144-48-9
Molecular Weight:
184.96
UNSPSC Code:
12352202
NACRES:
NA.77
PubChem Substance ID:
24278486
EC Number:
205-630-1
Beilstein/REAXYS Number:
1739080
MDL number:
MFCD00008028
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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

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.
Iodoacetamide acts as an alkylating reagent for cysteine residues in peptide sequencing. It is an irreversible inhibitor of enzymes with cysteine at the active site. It reacts much more slowly with histidine residues, but that activity is responsible for inhibiting ribonuclease.

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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

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

I1149-5G:4.548173990675E12 + I1149-25G:4.548173990668E12 + I1149-100G:4.548173990682E12

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Certificates of Analysis (COA)

Lot/Batch Number
0000550504
0000550504
0000526116
0000526116
0000488186

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Product Information Sheet - I1149
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
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