Iodoacetamide

Iodoacetamide
Skeletal formula
Space-filling model
Names
Preferred IUPAC name
2-Iodoacetamide
Other names
IAA[1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.119 Edit this at Wikidata
EC Number
  • 205-630-1
RTECS number
  • AC4200000
UNII
  • 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)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 0: Will not burn. E.g. waterInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
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).
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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.

  1. ^ Krüger, Ralf; Hung, Chien-Wen; Edelson-Averbukh, Marina; Lehmann, Wolf D. (2005). "Iodoacetamide-alkylated methionine can mimic neutral loss of phosphoric acid from phosphopeptides as exemplified by nano-electrospray ionization quadrupole time-of-flight parent ion scanning". Rapid Communications in Mass Spectrometry. 19 (12). Wiley: 1709–1716. Bibcode:2005RCMS...19.1709K. doi:10.1002/rcm.1976. ISSN 0951-4198. PMID 15912474.
  2. ^ Smythe CV (1936). "The reactions of Iodoacetate and of Iodoacetamide with various Sulfhydryl groups, with Urease, and with Yeast preparations". J. Biol. Chem. 114 (3): 601–12. doi:10.1016/S0021-9258(18)74789-3.
  3. ^ Anson ML (1940). "The reactions of Iodine and Iodoacetamide with native Egg Albumin". J. Gen. Physiol. 23 (3): 321–31. doi:10.1085/jgp.23.3.321. PMC 2237930. PMID 19873158.