Iodoacetamide

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Iodoacetamide
Skeletal formula
Skeletal formula
Space-filling model
Space-filling model
Names
Preferred IUPAC name
2-Iodoacetamide
Other names
IAA[1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
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EC Number
  • 205-630-1
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RTECS number
  • AC4200000
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5) checkY
    Key: PGLTVOMIXTUURA-UHFFFAOYSA-N checkY
  • InChI=1/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5)
    Key: PGLTVOMIXTUURA-UHFFFAOYAE
  • C(C(=O)N)I
Properties
ICH2CONH2
Molar mass 184.964 g·mol−1
Appearance white crystals (yellow colouration indicates the presence of iodine)
Melting point 94 °C (201 °F; 367 K)
Hazards
NFPA 704 (fire diamond)

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3
0
1
Safety data sheet (SDS) MSDS 1, MSDS 2
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Iodoacetamide (IAA) is an organic compound with the chemical formula ICH2CONH2. It is an alkylating agent used for peptide mapping purposes. Its actions are similar to those of iodoacetate. It is commonly used to bind covalently with the thiol group of cysteine so the protein cannot form disulfide bonds.[2][3] It is also used in ubiquitin studies as an inhibitor of deubiquitinase enzymes (DUBs) because it alkylates the cysteine residues at the DUB active site.

Peptidase inhibitor

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Iodoacetamide is an irreversible inhibitor of all cysteine peptidases, with the mechanism of inhibition occurring from alkylation of the catalytic cysteine residue (see schematic). In comparison with its acid derivative, iodoacetate, iodoacetamide reacts substantially faster. This observation appears contradictory to standard chemical reactivity, however the presence of a favourable interaction between the positive imidazolium ion of the catalytic histidine and the negatively charged carboxyl-group of the iodoacetate is the reason for the increased relative activity of iodoacetamide.[4]

File:Iodoacetamide mech wiki.png
Mechanism of irreversible inhibition of cysteine peptidases with iodoacetamide.

Protein mass spectrometry

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It is commonly used during the sample preparation for de novo (peptide) sequencing with protein mass spectrometry, but recent critics suggest to avoid the use of it [5]

References

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  • The MEROPS online database for peptidases and their inhibitors: [1]
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