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Key Documents

I6125

Sigma-Aldrich

Iodoacetamide

≥99% (NMR), crystalline

Synonym(s):

α-Iodoacetamide, 2-Iodoacetamide

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About This Item

Linear Formula:
ICH2CONH2
CAS Number:
Molecular Weight:
184.96
Beilstein:
1739080
EC Number:
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

Assay

≥99% (NMR)

form

crystalline

mp

92-95 °C (lit.)

solubility

H2O: soluble 0.5 M, clear, colorless

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


  • A Mass Spectrometry Strategy for Protein Quantification Based on the Differential Alkylation of Cysteines Using Iodoacetamide and Acrylamide.: This study presents a novel mass spectrometry method for quantifying proteins by differentially alkylating cysteines with iodoacetamide and acrylamide, enhancing the accuracy of protein quantification in complex samples. (Virág et al., 2024).

  • Laminarin ameliorates iodoacetamide-induced functional dyspepsia via modulation of 5-HT(3) receptors and the gut microbiota.: Research demonstrates that laminarin can mitigate functional dyspepsia induced by iodoacetamide through modulating 5-HT(3) receptors and altering gut microbiota composition, offering potential therapeutic benefits. (Liu et al., 2024).

  • Redox proteomics in melanoma cells: An optimized protocol.: This paper describes an optimized redox proteomics protocol using iodoacetamide, which facilitates the identification of redox-sensitive proteins in melanoma cells, aiding in the understanding of redox regulation in cancer. (Cunha et al., 2024).

  • Molecular targets of cisplatin in HeLa cells explored through competitive activity-based protein profiling strategy.: Utilizing iodoacetamide in competitive activity-based protein profiling, this study identifies molecular targets of cisplatin in HeLa cells, providing insights into the drug′s mechanisms. (Chen et al., 2024).

  • Development and Comparison of 4-Thiouridine to Cytidine Base Conversion Reaction.: This research compares base conversion reactions involving 4-thiouridine and cytidine, with iodoacetamide playing a crucial role in the reaction mechanism, contributing to advancements in nucleotide chemistry. (Ohashi et al., 2024).

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.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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