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Iodoacetamide (IAA) is an organic compound with the chemical formula I C H 2 CO NH 2. 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.
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. In 1929, Dr. Einar Lundsgaard (1899-1968) discovered that muscle poisoned in vitro with iodoacetic acid is unable to produce lactate as glycolysis from muscle glycogen is blocked ...
In course of the subsequent irreversible alkylation of the SH groups with iodoacetamide the cysteines are transformed to the stable S-carboxyamidomethylcysteine (CAM; adduct: -CH 2-CONH 2). The molecular weight of the cysteine amino-acid residue is thereby increased from 103.01 Da to 160.03 Da.
Initial treatment is with adequate hydration, alkalization of the urine with citrate supplementation or acetazolamide, and dietary modification to reduce salt and protein intake (especially methionine). If this fails then patients are usually started on chelation therapy with an agent such as penicillamine. [8] [9] Tiopronin is another agent ...
It contains the amide functional group, but more importantly it is an alkene that is reactive toward thiols and is commonly used to modify cysteine residues in proteins and peptides. [ 2 ] Organic chemistry
The formation of disulfide bonds from cysteine residues may also be referred to as a post-translational modification. [3] For instance, the peptide hormone insulin is cut twice after disulfide bonds are formed, and a propeptide is removed from the middle of the chain; the resulting protein consists of two polypeptide chains connected by ...
The site-directed covalent warhead, also called a covalent modifier, is an electrophile that covalently modifies a serine, cysteine, or lysine residue in the enzyme's active site and prevents future interactions with other ligands. [7]
The US list price of eteplirsen is US$300,000 per year of treatment citation needed. The Institute for Clinical and Economic Review has found the drug not cost effective at the list price when the cost of one Quality-adjusted life year (QALY) was equal to US$150,000. [20]