Iodoacetamide

Iodoacetamide

Names
IUPAC name Iodoacetamide
Identifiers
CAS Number	144-48-9 Y
3D model (JSmol)	Interactive image
ChemSpider	3596 Y
ECHA InfoCard	100.005.119
EC Number	205-630-1
IUPHAR/BPS	6271
PubChem CID	3727
RTECS number	AC4200000
UNII	ZRH8M27S79 Y
InChI InChI=1S/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5) Y Key: PGLTVOMIXTUURA-UHFFFAOYSA-N Y InChI=1/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5) Key: PGLTVOMIXTUURA-UHFFFAOYAE
SMILES C(C(=O)N)I
Properties
Chemical formula	C2H4INO
Molar mass	184.96 g·mol−1
Appearance	white crystals (yellow colouration indicates the presence of iodine)
Melting point	94 °C (201 °F; 367 K)
Hazards
Safety data sheet	brief MSDS, extended MSDS
NFPA 704	0 3 1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

2-Iodoacetamide 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. Also used in ubiquitin studies as an inhibitor of deubiquitinase enzymes (DUBs) because it alkylates the cysteine residues at the DUB active site.

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 more quickly. 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.