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A3221

Sigma-Aldrich

Iodoacetamide

Single use vial of 56 mg

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Synonym(s):
2-Iodoacetamide, IAA, Monoiodoacetamide, alpha-Iodoacetamide
Linear Formula:
ICH2CONH2
CAS Number:
Molecular Weight:
184.96
Beilstein:
1739080
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.56

Assay

≥99% (HPLC)

form

powder

packaging

vial of 56 mg (Single use)

mp

92-95 °C (lit.)

solubility

H2O: soluble 50 mg/mL, clear, colorless to faintly yellow

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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This Item
I1149I6125407710
Iodoacetamide Single use vial of 56 mg

Sigma-Aldrich

A3221

Iodoacetamide

-
Iodoacetamide BioUltra

Sigma-Aldrich

I1149

Iodoacetamide

Premium Grade
Iodoacetamide ≥99% (NMR), crystalline

Sigma-Aldrich

I6125

Iodoacetamide

-
Sigma-Aldrich

Sigma-Aldrich

407710

α-Iodoacetamide

-
form

powder

form

powder

form

crystalline

form

crystalline solid

mp

92-95 °C (lit.)

mp

92-95 °C (lit.)

mp

92-95 °C (lit.)

mp

-

solubility

H2O: soluble 50 mg/mL, clear, colorless to faintly yellow

solubility

H2O: 0.5 M, clear, colorless

solubility

H2O: soluble 0.5 M, clear, colorless

solubility

methanol: 1:20, DMF: soluble, ethanol: soluble, water: soluble

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

Quality Level

200

Quality Level

300

Quality Level

300

Quality Level

200

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
  • to inhibit glyceraldehyde-3-phosphate dehydrogenase effectively blocking ATP production in cell biology research

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

Packaged in sealed ampules

Legal Information

Technology developed in partnership with Proteome Systems
Proteome Systems is a trademark of Proteome Systems Ltd

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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

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Kristen L Koterba et al.
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During large-scale manufacturing of an IgG1 monoclonal antibody in Chinese hamster ovary (CHO) cells, reduction of the antibody's disulfide bonds was observed. We present evidence that mammalian thioredoxin 1 (TXN1) is the terminal enzyme responsible for this reduction event. We
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Valentina R Minciacchi et al.
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