iodoacetamide

{{chembox

|Watchedfields = changed

|verifiedrevid = 443876177

|ImageFile = Iodoacetamide.png

|ImageName = Skeletal formula

|ImageFile1 = Iodoacetamide-3D-vdW.png

|ImageName1 = Space-filling model

|PIN = 2-Iodoacetamide

|OtherNames = IAA{{cite journal | last1=Krüger | first1=Ralf | last2=Hung | first2=Chien-Wen | last3=Edelson-Averbukh | first3=Marina | last4=Lehmann | first4=Wolf D. | title=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 | journal=Rapid Communications in Mass Spectrometry | publisher=Wiley | volume=19 | issue=12 | year=2005 | issn=0951-4198 | doi=10.1002/rcm.1976 | pages=1709–1716| pmid=15912474 | bibcode=2005RCMS...19.1709K}}

|Section1 = {{Chembox Identifiers

|IUPHAR_ligand = 6271

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 3596

|InChI = 1/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5)

|InChIKey = PGLTVOMIXTUURA-UHFFFAOYAE

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|ChEMBL = 276727

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

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

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = PGLTVOMIXTUURA-UHFFFAOYSA-N

|CASNo_Ref = {{cascite|correct|CAS}}

|CASNo = 144-48-9

|PubChem = 3727

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = ZRH8M27S79

|SMILES = C(C(=O)N)I

|RTECS = AC4200000

|EINECS = 205-630-1

}}

|Section2={{Chembox Properties

|Formula = {{chem2|ICH2CONH2}}

|C=2|H=4|I=1|N=1|O=1

|Appearance = white crystals (yellow colouration indicates the presence of iodine)

|Density =

|MeltingPtC = 94

|BoilingPt =

|Solubility =

}}

|Section7={{Chembox Hazards

|FlashPt =

|AutoignitionPt =

|ExternalSDS = [https://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=CA&language=en&productNumber=I6709&brand=ALDRICH MSDS 1], [https://www.msdsdigital.com/iodoacetamide-msds-2 MSDS 2]

|NFPA-H = 3

|NFPA-F = 0

|NFPA-R = 1

}}

|Section8={{Chembox Related

|OtherCompounds = {{ubl|Acetamide|Fluoroacetamide|Chloroacetamide|Bromoacetamide|Iodoacetic acid}}

}}

}}

Iodoacetamide (IAA) is an organic compound with the chemical formula {{chem2|ICH2CONH2|auto=1}}. 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.{{cite journal |author=Smythe CV|title=The reactions of Iodoacetate and of Iodoacetamide with various Sulfhydryl groups, with Urease, and with Yeast preparations|journal=J. Biol. Chem.|volume=114|issue=3 |pages=601–12 |year=1936|doi=10.1016/S0021-9258(18)74789-3|url=http://www.jbc.org/content/114/3/601.full.pdf+html?sid=60fb7e03-5a4f-42fb-bd4e-3f86772cdc9d|doi-access=free}}{{cite journal|doi=10.1085/jgp.23.3.321|author=Anson ML |title=The reactions of Iodine and Iodoacetamide with native Egg Albumin|journal=J. Gen. Physiol. |volume=23|issue=3|pages=321–31|year=1940|pmid=19873158|pmc=2237930}} 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.