Iodoacetamide

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Iodoacetamide


IUPAC name Iodoacetamide
Identifiers
CAS number	144-48-9^Y
PubChem	3727
ChemSpider	3596^Y
UNII	ZRH8M27S79^Y
EC number	205-630-1
ChEMBL	CHEMBL276727^Y
RTECS number	AC4200000
Jmol-3D images	Image 1
SMILES C(C(=O)N)I
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
Properties
Molecular 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
MSDS	brief MSDS, extended MSDS
NFPA 704	0 3 1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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.^[1]^[2] 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

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.^[3]

Mechanism of irreversible inhibition of cysteine peptidases with iodoacetamide.

References

↑ 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.
↑ 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.
↑ Polgar, L (1979). "Deuterium isotope effects on papain acylation. Evidence for lack of general base catalysis and for enzyme-leaving group. interaction". Eur. J. Biochem. 98 (2): 369–374. doi:10.1111/j.1432-1033.1979.tb13196.x. PMID 488108.

External links

The MEROPS online database for peptidases and their inhibitors: Iodoacetamide

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