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Merck
CN

57670

Sigma-Aldrich

Iodoacetamide

≥98.0% (AT), purum

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About This Item

Linear Formula:
ICH2CONH2
CAS Number:
144-48-9
Molecular Weight:
184.96
Beilstein:
1739080
EC Number:
205-630-1
MDL number:
MFCD00008028
UNSPSC Code:
12352202
eCl@ss:
32035301
PubChem Substance ID:
329758332

Key Documents

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grade

purum

Assay

≥98.0% (AT)

mp

92-95 °C (lit.)
92-95 °C

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

May contain some chloracetamide.

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.

Other Notes

Thiol reagent. Carboxymethylation

Disclaimer

May discolor to yellowish on storage.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H317,H334,H413

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

Regulatory Information

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[34a] carboxymethylation.
F R Gurd
Methods in enzymology, 25, 424-438 (1972-01-01)
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)
Chiara Francavilla et al.
The Journal of cell biology, 187(7), 1101-1116 (2009-12-30)
Neural cell adhesion molecule (NCAM) associates with fibroblast growth factor (FGF) receptor-1 (FGFR1). However, the biological significance of this interaction remains largely elusive. In this study, we show that NCAM induces a specific, FGFR1-mediated cellular response that is remarkably different
Mia Jüllig et al.
PloS one, 9(5), e96489-e96489 (2014-05-08)
Bypass of foregut secreted factors promoting insulin resistance is hypothesized to be one of the mechanisms by which resolution of type 2 diabetes (T2D) follows roux-en-y gastric bypass (GBP) surgery. To identify insulin resistance-associated proteins and metabolites which decrease more
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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