Iodoacetic acid

It is often used to modify −SH groups to prevent the re-formation of disulfide bonds after the reduction of cystine residues to cysteine during protein sequencing.

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 iodoacetic acid is the reason for the increased activity of iodoacetamide.

In 2002 Fawzia Fahim showed that "a single IAA treatment of tumor-bearing mice significantly increased the levels of plasma lactate dehydrogenase (LDH) activity, while it also significantly decreased the levels of plasma glucose and liver total protein, RNA and DNA, compared to normal controls.

"[7] In 1975 Melvin S. Rhein, Joyce A. Filppi and Victor S. Moore showed that iodoacetate improved the immune response of bone marrow.

[9] Iodide is a naturally occurring ion that can be found in many source waters and it is easily oxidized by wastewater disinfectants.

Skeletal formula
Skeletal formula
Space-filling model
Space-filling model
Mechanism of irreversible inhibition of cysteine peptidases with iodoacetate.