Back یدواستامید AZB Iodacetamid German Jodoacetamido Esperanto یدواستامید Persian Jodiasetamidi Finnish Iodoacétamide French ヨードアセトアミド Japanese Joodaceetamide Dutch Jodoacetamid Serbo-Croatian Jodoacetamid Serbian
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| Names | |
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| Preferred IUPAC name
2-Iodoacetamide | |
| Other names
IAA[1]
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.005.119 |
| EC Number |
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PubChem CID
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| RTECS number |
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| UNII | |
CompTox Dashboard (EPA)
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| 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) | |
| Safety data sheet (SDS) | MSDS 1, MSDS 2 |
| Related compounds | |
Related compounds
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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.
- ^ 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.
- ^ 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.
- ^ 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.