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A3221

Sigma-Aldrich

Iodoacétamide

Single use vial of 56 mg

Synonyme(s) :

2-Iodoacetamide, IAA, Monoiodoacetamide, alpha-Iodoacetamide

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About This Item

Formule linéaire :
ICH2CONH2
Numéro CAS:
144-48-9
Poids moléculaire :
184.96
Numéro Beilstein :
1739080
Numéro CE :
205-630-1
Numéro MDL:
MFCD00008028
Code UNSPSC :
12352111
ID de substance PubChem :
24890731
Nomenclature NACRES :
NA.56

Source biologique

synthetic (organic)

Pureté

≥99% (HPLC)

Forme

powder

Conditionnement

vial of 56 mg (Single use)

Conditions de stockage

(Tightly closed. Dry. Keep in a well-ventilated place. Keep locked up or in an area accessible
only to qualified or authorized persons.)

Couleur

white to off-white

Pf

92-95 °C (lit.)

Solubilité

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

Adéquation

suitable for LC-MS

Application(s)

microbiology

Température de stockage

2-8°C

Chaîne SMILES 

NC(=O)CI

InChI

1S/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5)

Clé InChI

PGLTVOMIXTUURA-UHFFFAOYSA-N

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Description générale

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

Actions biochimiques/physiologiques

L'iodoacétamide agit comme un réactif d'alkylation des résidus cystéine pour le séquençage des peptides. C'est un inhibiteur irréversible des enzymes présentant une cystéine au niveau de leur site actif. Il réagit beaucoup plus lentement avec les résidus histidine, mais cette activité entraîne l'inhibition de la ribonucléase.

Caractéristiques et avantages

High quality compound suitable for multiple research applications

Conditionnement

Packaged in sealed ampules

Autres remarques

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

Informations légales

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

Produit comparable

Réf. du produit
Description
Tarif

I1149

Iodoacétamide, BioUltra

I6125

Iodoacétamide, ≥99% (NMR), crystalline

Souvent commandé avec ce produit

Réf. du produit
Description
Tarif

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H301,H317,H334,H413

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Kristen L Koterba et al.
Journal of biotechnology, 157(1), 261-267 (2011-12-06)
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
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)
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
Elena B Lugli et al.
Arthritis research & therapy, 17, 9-9 (2015-01-21)
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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