A3221

Iodoacetamide

Single use vial of 56 mg

• Synonym(s): 2-Iodoacetamide, IAA, Monoiodoacetamide, alpha-Iodoacetamide
• Linear Formula: ICH₂CONH₂
• CAS Number: 144-48-9
• Molecular Weight: 184.96
• UNSPSC Code: 12352111
• NACRES: NA.56
• PubChem Substance ID: 24890731
• EC Number: 205-630-1
• Beilstein/REAXYS Number: 1739080
• MDL number: MFCD00008028

Properties

• biological source: synthetic (organic)
• Quality Level: 200
• assay: ≥99% (HPLC)
• form: powder
• packaging: vial of 56 mg (Single use)
• storage condition: (Tightly closed. Dry. Keep in a well-ventilated place. Keep locked up or in an area accessible; only to qualified or authorized persons.)
• color: white to off-white
• mp: 92-95 °C (lit.)
• solubility: H₂O: soluble 50 mg/mL, clear, colorless to faintly yellow
• suitability: suitable for LC-MS
• application(s): microbiology
• 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

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.

Application

Iodoacetamide has been used:

• to prevent enzymatic disulfide reduction in the protein samples[1]
• to inhibit glyceraldehyde-3-phosphate dehydrogenase effectively blocking ATP production in cell biology research[1]

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.

Packaging

20 mL white HDPE bottle with 22-410H red PP cap, inside 5 mL glass vial.

Other Notes

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Legal Information

Technology developed in partnership with Proteome Systems^™

Proteome Systems is a trademark of Proteome Systems Ltd

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
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges