Iodoacetamide
SIGMA/A3221 - Single use vial of 56 mg
Synonym: 2-Iodoacetamide; IAA; Monoiodoacetamide; alpha-Iodoacetamide
CAS Number: 144-48-9
Empirical Formula (Hill Notation): C2H4INO
Molecular Weight: 184.96
EC Number: 205-630-1
MDL Number: MFCD00008028
Linear Formula: ICH2CONH2
Product Type: Chemical
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: A3221-1VL.
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: A3221-5VL.
| application(s) | microbiology |
| assay | ≥99% (HPLC) |
| biological source | synthetic (organic) |
| color | white to off-white |
| form | powder |
| InChI | 1S/C2H4INO/c3-1-2(4)5/h1H |
| InChI key | PGLTVOMIXTUURA-UHFFFAOYSA |
| mp | 92-95 °C (lit.) |
| packaging | vial of 56 mg (Single use) |
| Quality Level | 200  |
| SMILES string | NC(=O)CI |
| solubility | H2O: soluble 50 mg/mL, clear, colorless to faintly yellow |
| storage condition | ( only to qualified or authorized persons. |
| storage temp. | 2-8°C |
| suitability | suitable for LC-MS |
| Application: | Iodoacetamide has been used: • to prevent enzymatic disulfide reduction in the protein samples • to inhibit glyceraldehyde-3-phosphat |
| Biochem/physiol Actions: | 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. |
| Features and Benefits: | High quality compound suitable for multiple research applications |
| General description: | 2-Iodoacetamide is a thiol-alkylating agent frequently used in peptide mapping for biochemical, cell culture and proteomics research. It functions similarly to iodoacetate, primarily binding covalently with the thiol group of cysteine in proteins, thereby preventing the formation of disulfide bonds. This attribute is crucial for several applications, including 2-D protein electrophoresis to reduce streaking and improve resolution, as an inhibitor of deubiquitinase enzymes (DUBs) and a peptidase inhibitor. It is often employed during sample preparation for de novo peptide sequencing with protein mass spectrometry. It has specific interactions with cysteine and histidine residues in proteins, affecting enzymes like ribonuclease. While it may react slowly with histidine, its inhibitory properties contribute to the research on proteases, such as cysteine proteases. Iodoacetamide is known for its irreversibility in inhibiting enzymes and its ability to form stable protein derivatives, making it valuable in studying protein structures, protein behavior, and enzyme inhibition. |
| Legal Information: | Proteome Systems is a trademark of Proteome Systems Ltd |
| Legal Information: | Technology developed in partnership with Proteome Systems™ |
| Other Notes: | For additional information on our range of Biochemicals , please complete this form . |
| Packaging: | 10 vials in glass insert |
| Packaging: | Packaged in sealed ampules |
| Symbol |  GHS06 |
| Signal word | Danger |
| Hazard statements | H301 - H315 - H317 - H319 - H335 |
| Precautionary statements | P261 - P264 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338 |
| Hazard Codes | T |
| Risk Statements | 25-42/43-53 |
| Safety Statements | 22-36/37-45 |
| RIDADR | UN 2811 6.1 / PGIII |
| WGK Germany | WGK 3 |
| Purity | ≥99% (HPLC) |
| mp | 92-95 °C (lit.) |
| Storage Temp. | 2-8°C |
| UNSPSC | 12352111 |