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A3221

Sigma-Aldrich

Iodoacetamide

Single use vial of 56 mg

Synonym(s):

2-Iodoacetamide, IAA, Monoiodoacetamide, alpha-Iodoacetamide

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About This Item

Linear Formula:
ICH2CONH2
CAS Number:
144-48-9
Molecular Weight:
184.96
Beilstein/REAXYS Number:
1739080
EC Number:
205-630-1
MDL number:
MFCD00008028
UNSPSC Code:
12352111
PubChem Substance ID:
24890731
NACRES:
NA.56

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

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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

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

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pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tanja Scherrer et al.
Genome biology, 12(1), R3-R3 (2011-01-15)
Glucose inhibition of gluconeogenic growth suppressor 2 protein (Gis2p) and zinc-finger protein 9 (ZNF9) are conserved yeast and human zinc-finger proteins. The function of yeast Gis2p is unknown, but human ZNF9 has been reported to bind nucleic acids, and mutations
Mirko Zaffagnini et al.
Antioxidants & redox signaling, 16(1), 17-32 (2011-06-29)
Cysteines (Cys) made acidic by the protein environment are generally sensitive to pro-oxidant molecules. Glutathionylation is a post-translational modification that can occur by spontaneous reaction of reduced glutathione (GSH) with oxidized Cys as sulfenic acids (-SOH). The reverse reaction (deglutathionylation)
Helen R Stagg et al.
The Journal of cell biology, 186(5), 685-692 (2009-09-02)
The US2 and US11 gene products of human cytomegalovirus promote viral evasion by hijacking the endoplasmic reticulum (ER)-associated degradation (ERAD) pathway. US2 and US11 initiate dislocation of newly translocated major histocompatibility complex class I (MHC I) from the ER to
Valentina R Minciacchi et al.
Oncotarget, 6(13), 11327-11341 (2015-04-11)
Large oncosomes (LO) are atypically large (1-10 µm diameter) cancer-derived extracellular vesicles (EVs), originating from the shedding of membrane blebs and associated with advanced disease. We report that 25% of the proteins, identified by a quantitative proteomics analysis, are differentially
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Smoking is a well-established risk factor for rheumatoid arthritis (RA), and it has been proposed that smoking-induced citrullination renders autoantigens immunogenic. To investigate this mechanism, we examined human lung tissue from 40 subjects with defined smoking status, with or without
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