Chemical Properties
white to light yellow crystalline powder
Uses
Used as a general reagent in acylation reactions. A byproduct formed in treated waters, and found in marine life.
Uses
Iodoacetic acid is used as a reagent for the modification of sulfhydryl groups in organic synthesis. It reacts with cysteine moiety in proteins to prevent the re-formation of disulfide bonds during protein sequencing. It is also used as a general reagent in acylation reactions as well as in glycopeptide synthesis.
Definition
ChEBI: A haloacetic acid that is acetic acid in which one of the hydrogens of the methyl group is replaced by an iodine atom.
General Description
Colorless or white crystals.
Air & Water Reactions
May be sensitive to heat, light, and air. Water soluble
Reactivity Profile
Iodoacetic acid reacts vigorously with bases and is corrosive.
Fire Hazard
Flash point data for Iodoacetic acid are not available, but Iodoacetic acid is probably non-flammable.
Biochem/physiol Actions
Iodoacetic acid (IAA) blocks the thiol group of cysteine. IAA inhibits glyceraldehyde-3-phosphate dehydrogenase (G3PDH) by interacting with sulfhydryl group of the active site cysteine. IAA inhibits the progression of solid Ehrlich carcinoma. IAA is one of the iodinated disinfection byproducts in drinking water. It is cytotoxic to mammalian cells.
Purification Methods
Crystallise it from pet ether (b 60-80o) or CHCl3/CCl4. [Beilstein 2 IV 534.]
