Skip to Content
Merck

A3221

Iodoacetamide

Single use vial of 56 mg

Synonym(s):

2-Iodoacetamide, IAA, Monoiodoacetamide, alpha-Iodoacetamide

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Linear Formula:
ICH2CONH2
CAS Number:
Molecular Weight:
184.96
UNSPSC Code:
12352111
NACRES:
NA.56
PubChem Substance ID:
EC Number:
205-630-1
Beilstein/REAXYS Number:
1739080
MDL number:
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist


biological source

synthetic (organic)

Quality Level

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

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

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

Other Notes

For additional information on our range of Biochemicals, please complete this form.

Legal Information

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


Still not finding the right product?

Explore all of our products under Iodoacetamide


pictograms

Skull and crossbonesHealth hazard

signalword

Danger

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



Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

It looks like we've run into a problem, but you can still download Certificates of Analysis from our Documents section.

If you need assistance, please contact Customer Support

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library