I1149

Iodoacetamide

BioUltra

• Synonym(s): 2-Iodoacetamide, Monoiodoacetamide, alpha-Iodoacetamide
• Linear Formula: ICH₂CONH₂
• CAS Number: 144-48-9
• Molecular Weight: 184.96
• Beilstein/REAXYS Number: 1739080
• EC Number: 205-630-1
• MDL number: MFCD00008028
• UNSPSC Code: 12352202
• PubChem Substance ID: 24278486
• NACRES: NA.77

Properties

• 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 (SO₄^2-): ≤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

Description

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.

Safety Information

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H301 - H317 - H334 - H413
• pcodes: P261 - P264 - P273 - P280 - P301 + P310 - P302 + P352
• 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