2-Iodoacetamide, also known as iodoacetamide or IAM, is a versatile organic compound belonging to the class of acetamides. This colorless to yellow liquid, characterized by its distinct odor, is widely utilized in various scientific and industrial applications due to its unique reactivity.
One of the primary applications lies in proteomics research, where it serves as an alkylating agent for cysteine residues in proteins. This reaction, known as carbamidomethylation, prevents disulfide bond reformation during sample preparation steps for proteomic analysis, enabling better preservation of protein structure and facilitating mass spectrometry-based protein identification and quantification.
In addition to its use in proteomics, it has found applications in the synthesis of bioactive compounds, owing to its ability to serve as a building block for introducing iodine, a biologically essential halogen, into organic molecules. It can also participate in click chemistry reactions, broadening its synthetic utility in the field of organic chemistry.
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Chemical Formula |
C2H4INO |
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Exact Mass |
184.93 |
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Molecular Weight |
184.96 |
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m/z |
184.93 (100.0%), 185.94 (2.2%) |
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Elemental Analysis |
C, 12.99; H, 2.18; I, 68.61; N, 7.57; O, 8.65 |
- Protein Modification: Commonly used as an alkylating agent in proteomics sample preparation, specifically for the alkylation of cysteine residues in proteins. This modification makes the cysteine residues less reactive and more stable during subsequent analytical procedures, such as trypsin digestion. By alkylating cysteines, it facilitates the accurate determination of amino acid sequences and enhances the identification of proteins in complex mixtures.
- Improved Peptide Identification: The alkylation of cysteine residues by 2-Iodoacetamide renders these amino acids less prone to artifactual modifications during sample handling and analysis. This improves the quality of proteomic data by reducing the number of false positives and enhancing the overall reliability of peptide identification.
- Peptide Sequencing: In addition to its use in proteomics, it is also employed in peptide sequencing. By alkylating cysteine residues, it helps stabilize peptides during the sequencing process, enabling researchers to obtain more accurate and reliable sequence information.
- Enzyme Inhibition: As an effective enzyme inhibitor, it can bind to the active sites of certain enzymes, thereby inhibiting their activity. This inhibitory effect is valuable in understanding enzyme mechanisms and facilitating drug design and development.
- Intermediate and Raw Material: Serving as an important intermediate and raw material in organic synthesis. Its unique chemical properties, particularly the reactivity of the iodine atom, make it a useful building block for the synthesis of various bioactive molecules.
- Structural Modification: The iodine atom in it can be easily substituted or modified, allowing researchers to introduce specific functional groups into target molecules. This capability makes it a valuable tool for structural modification and optimization of bioactive compounds.
- Protein Structure and Function: By alkylating cysteine residues in proteins, it enables researchers to study the structure and function of these proteins in more detail. The modification can affect protein stability, folding, and interactions with other molecules, providing valuable insights into protein biology.
- Inhibitor Design: The inhibitory effect on enzymes can be exploited in the design of new inhibitors. By modifying the structure, researchers can create potent and selective inhibitors that target specific enzymes involved in disease processes.
It is an important chemical reagent that is widely used in many fields such as proteomics, peptide sequencing, and enzyme inhibitors. Its synthesis is mainly carried out by the reaction of chloroacetamide and sodium iodide. The following is a detailed synthesis and preparation method:
principle
The synthesis of 2-Iodoacetamide is based on a halogen exchange reaction, where the chlorine atom in chloroacetamide is replaced by an iodine atom.
Reactants & Reagents
1
as the main raw material of the reaction.
2
as the reaction solvent, it helps the reactants to mix and react fully.
3
provides iodine atoms to exchange with the chlorine atoms in chloroacetamide.
4
used for subsequent treatment and purification steps.
steps
Mixing reactants: Chloroacetamide, anhydrous acetone and anhydrous sodium iodide are mixed in a reaction vessel in a certain proportion.
Heating and reflux: The mixture is refluxed under heating conditions for a period of time (usually 15 hours) to ensure that the reaction is fully carried out.
Cooling and filtering: After the reaction is completed, the mixture is cooled to room temperature and the generated sodium chloride solid is filtered out.
Recovering the solvent: Recover and treat the reaction solvent acetone for reuse or safe disposal.
Neutralization and crystallization: After the filtrate is cooled slightly, it is poured into ice water of sodium bisulfate and then neutralized to pH 6 with a saturated sodium sulfate solution. Then cool and crystallize, and filter to obtain a crude product.
Recrystallization: The crude product is recrystallized with water to further purify the product and finally obtain high-purity product.
In vivo studies, the toxic effects have been explored in detail, especially in long-term exposure experiments conducted in animal models. These studies usually use rats as experimental subjects to evaluate the potential effects of the compound on organisms.
Experimental models and conditions
- Animal model: Sprague-Dawley rats
- Dosage: 2.0-10 mg
- Administration: Daily administration through drinking water
- Duration: 20 to 93 days
Experimental results
In these experiments, the main results observed were:
- Gastritis production: Many experimental rats developed inflammation of the stomach (gastritis) after exposure to 2-Iodoacetamide.
- Chronic ulcers: Further studies found that these gastritis further complicated with chronic deep ulcers in many rats, mainly in the secretory part of the stomach.
Safety and toxicity assessment
These in vivo findings highlight the potential toxicity in organisms, especially in the case of long-term exposure. Therefore, when using this compound for biological research, it is necessary to be cautious and strictly control the experimental conditions to ensure the safety of experimental animals and the reliability of experimental results.
Storage and handling
Since it is sensitive to light and moisture, its storage conditions are also particularly important. It is generally recommended to store it in a sealed container at 2-8°C, away from light sources and moisture. In addition, when handling this compound, appropriate protective equipment, such as protective gloves and respiratory protective equipment, should be worn to avoid inhalation of dust or vapor.
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