144-48-9

Usage

Uses

Used in Peptide Sequencing:
2-Iodoacetamide is used as an alkylating agent for cysteine residues in peptide mapping. It covalently binds with the thiols in cysteine to prevent disulfide bond formation, which is crucial for the accurate sequencing and analysis of peptides.
Used in Enzyme Inhibition:
2-Iodoacetamide is used as an electrophile for covalent modification of nucleophilic residues on proteins, such as cysteine, methionine, and histidine. By binding with the thiol group of cysteine, it protects the formation of disulfide bonds and acts as an irreversible inhibitor of enzymes with cysteine at their active sites.
Used in Deubiquitinase Enzyme Inhibition:
2-Iodoacetamide is involved as an inhibitor of deubiquitinase enzymes (DUBs), which play a role in various cellular processes, including protein degradation and signaling pathways. Its alkylating properties make it a useful tool for studying the function and regulation of these enzymes.
Used in Protein Modification:
2-Iodoacetamide acts as an alkylating sulfhydryl reagent, allowing for the covalent modification of proteins. This modification can be used to study protein structure, function, and interactions, as well as to develop new therapeutic strategies targeting specific proteins.

Synthesis

2-Iodoacetamide is synthesized by reacting chloroacetamide with sodium iodide. The chloroacetamide, anhydrous acetone, and anhydrous sodium iodide were refluxed on the bath for 15h. Cool to room temperature, filter out sodium chloride, recover acetone, pour into ice water of sodium bisulfate after a little cooling, and then neutralize to pH 6 with saturated sodium sulfate solution. Cool to crystallize and filter to obtain crude product. The crude product is recrystallized with water to obtain the finished product.

Purification Methods

Crystallise it from water or CCl4. It is used for tagging proteins. [Gurd Methods Enzymol 25 424 1972, Beilstein 2 IV 536.]

Preparation and handling

Alkylation ProcedureIodoacetamide is unstable and light-sensitive. Prepare solutions immediately before use and perform alkylation in the dark. If iodoacetamide is present in limiting quantities and a slightly alkaline pH, cysteine modification will be the exclusive reaction. Excess iodoacetamide or non-buffered iodoacetamide reagent can also alkylate amines (lysine, N-termini), thioethers (methionine), imidazoles (histidine) and carboxylates (aspartate, glutamate).1. Add 5 μl of 2% SDS and 45 μl of 200 mM ammonium bicarbonate (pH 8.0) to 20-100 μg of protein sample. Adjust volume to 100 μl with ultrapure water.2. Add 5 μl of 200 mM Tris(2-carboxyethyl) phosphine hydrochloride (TCEP.HCl, Product No. 20490) and incubate sample at 55°C for 1 hour.3. Immediately before use, dissolve one tube of iodoacetamide (9.3 mg) with 132 μl of 200 mM ammonium bicarbonate (pH 8.0) to make 375 mM iodoacetamide. Protect solution from light.4. Add 5 μl of the 375 mM iodoacetamide to the sample and incubate for 30 minutes protected from light.5. Proceed to proteolytic digestion before MS analysis or other processing.

Precautions

Store in a cool place. Light and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong acids, strong bases, strong oxidizing agents and strong reducing agents.

InChI:InChI=1/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5)

Upstream product

• 79-07-2 Chloroacetamide 
• 624-75-9 iodoacetonitrile 
• 64-17-5 ethanol 
• 107-91-5 cyanoacetic acid amide 
• 54907-61-8 iodoacetic anhydride 

Downstream Products

• 17528-66-4 cysteine 
• 123-93-3 thiodiacetic acid 
• 505-73-7 disulfanediyldiacetic acid 
• 13330-87-5 2(Acetamido)thioessigsaeure 
• 24466-68-0 Methylsulfonyloxy-acetamid 
• 24625-62-5 Diphenyl-dithiophosphinigsaeure-aminocarbonylmethylester 
• 111853-33-9 2-carbamoylmethylthio-6-methyl-4-phenyl-5-ethoxycarbonyl-3-cyano-1,4-dihydropyridine 
• 142847-17-4 Nα-1,1-dimethylethoxycarbonylasparagine 
• 66977-75-1 4-carbamoylmethyl-1,7,11-tritosyl-1,4,7,11-tetraazacyclotetradecane 
• 122275-72-3 5'-oxo-1,3,3-trimethyl-1,3-dihydrospiro<2H-indole-2,2'-pyrrolidine> 
• 5418-63-3 1,2,3,3-tetramethyl-3H-indolium iodide 
• 127871-14-1 2-[4-(4-Chloro-phenyl)-3-cyano-5-oxo-4,5-dihydro-1H-indeno[1,2-b]pyridin-2-ylsulfanyl]-acetamide 
• 127871-03-8 2-[(4S,4aR)-3-Cyano-9b-hydroxy-4-(4-nitro-phenyl)-5-oxo-4,4a,5,9b-tetrahydro-1H-indeno[1,2-b]pyridin-2-ylsulfanyl]-acetamide 
• 122275-78-9 3,3-dimethyl-5'-oxo-1-ethyl-1,3-dihydrospiro<2H-indole-2,2'-pyrrolidine> 

Relevant academic research and scientific papers

Effects of N-Substitutions on the Tetrahydroquinoline (THQ) Core of Mixed-Efficacy μ-Opioid Receptor (MOR)/δ-Opioid Receptor (DOR) Ligands

N-Acetylation of the tetrahydroquinoline (THQ) core of a series of μ-opioid receptor (MOR) agonist/δ-opioid receptor (DOR) antagonist ligands increases DOR affinity, resulting in ligands with balanced MOR and DOR affinities. We report a series of N-substituted THQ analogues that incorporate various carbonyl-containing moieties to maintain DOR affinity and define the steric and electronic requirements of the binding pocket across the opioid receptors. 4h produced in vivo antinociception (ip) for 1 h at 10 mg/kg.

The modified trifluoromethylation protocol applicable to electronically deficient iodopyridinones

Utilization of a mixed solvent system of DMF/HMPA=1/1 (v/v) to the KF/CuI/TMSCF3 reagent system proved to significantly affect the reaction, realizing convenient introduction of a trifluoromethyl (CF3) group not only to electron-deficient iodopyridinones with quite a few previous successful examples but also to aliphatic vinylic iodides.

Reactive derivatives of sulforhodamine 101 with enhanced hydrolytic stability

The invention describes reactive dyes having an alkyl spacer attached via a sulfonamide bond to a sulforhodamine 101 fluorophore, and a variety of useful conjugates prepared therefrom. The increased length of the covalent linkage due to the alkyl spacer results in dye-conjugates having a number of surprisingly advantageous properties relative to previous sulforhodamine 101-labeled conjugates, including enhanced solubility and increased fluorescence. The reactive dyes of the present invention are more stable than the known compound sulforhodamine 101 sulfonyl chloride. Novel reactive dyes are described for selective modification of groups other than amines, including thiols and photoreactive derivatives.

POLYHYDROXY BENZOIC ACID DERIVATIVES AND THEIR USE AS NEURAMINIDASE INHIBITORS

The present invention is directed to compositions of the formula: wherein: R2 is H, or an alkyl group having 1 to 3 carbon atoms and 0 to 2 hydroxyls; R3 is H, or hydroxyl; R4 is H, or forms a hydrolyzable ester or amide with -C02-; R5 are H, or are taken together to form =NH; and R6 comprises an amine, or a group having 1 to 12 carbon atoms and 1 to 3 amine groups. The invention is also directed to methods of inhibiting the activity of neuraminidase using the compounds of the invention

Scavenger assisted combinatorial process for preparing libraries of tertiary amine compounds

This invention relates to a novel solution phase process for the preparation of tertiary amine combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.

Cephem compound, process for producing the compound, and antimicrobial composition containing the same

The present invention provides a cephem compound having a high antimicrobial activity against various pathogenic bacteria. The cephem compound of the invention is represented by the formula STR1 wherein Q represents CH or N, R1 represents a carboxylate or the like, R2 represents a hydrogen atom, and R represents STR2 wherein R3 represents a group --(CH2)m --Y (wherein m is an integer of 1 to 5, and Y represents a quaternary ammonium group) or the like, n is an integer of 0 to 4, B- represents an anion, f is 0 or 1 when R1 represents a carboxylate, and 2 when R1 represents a carboxyl group, and the ring C represents a 5-membered heterocyclic group of not more than 4 nitrogen atoms, which may be substituted by a lower alkyl group.

Preparation process of aminoacetamide derivative

Disclosed herein are novel processes for preparing aminoacetamide derivatives, wherein: (1) a secondary amine is reacted with a 2-haloacetamide in the presence or absence of at least one solvent selected from water, lower alcohols, aromatic solvents and acetic acid esters; (2) an N-benzylideneamine derivative is reacted with dimethyl sulfate or diethyl sulfate to form a secondary amine, and this secondary amine is then reacted with a 2-haloacetamide; and (3) a primary amine is reacted with benzaldehyde to form an N-benzylideneamine derivative, this product is then reacted with dimethyl sulfate or diethyl sulfate to form a secondary amine, and this secondary amine is further reacted with a 2-haloacetamide. The 2-aminoacetamide derivatives are useful as intermediates for the preparation of novel antibiotics.

Reactive derivatives of bapta used to make ion-selective chelators

The invention relates to fluorescent and/or reactive derivatives of 1,2-bis-(2-aminophenoxyethane)-N,N,N',N'-tetraacetic acid (BAPTA) according to the formula: STR1 where at least one of W and X is a functional group, with or without a spacer, that terminates in an alcohol or phenol, a thiol, a haloacetamide, an alkyl halide, an amine or aniline, a carboxylic acid, an anhydride, an isocyanate, an isothiocyanate, a maleimide, or an activated ester. The BAPTA-like molecule may be further substituted, one or more times, by additional functional groups with or without spacers or by CH3, NO2, CF3, F, Cl, Br, I, or carboxylic acid derivatives or pharmaceutically acceptable salts thereof, or by indolyl or benzofuran fluorophores. The functional groups allow for subsequent covalent attachment of one or more oxygen heterocycle fluorophores (e.g. fluorescein, coumarin, rhodamine); or polymolecular assemblies (e.g. gel and resin polymers, polysaccharides, polypeptides, nucleic acids, and liposomes); or combinations thereof.

Long wavelength chemically reactive dipyrrometheneboron difluoride dyes and conjugates

This invention relates to derivatives of dipyrrometheneboron difluoride fluorescent dyes that have an absorption maximum at wavelengths longer than about 525 nm, and are chemically reactive with nucleic acids, proteins, carbohydrates, and other biologically derived or synthetic chemical materials. The dyes generally have the structure: STR1 wherein at least one of the substituents R1 -R7, is a reactive functional group, and at least one of the substituents R1 -R7 contains a bathochromic moiety. The bathochromic moiety is an unsaturated organic group, preferably heteroaryl or alkenyl. The remaining substituents, which may be the same or different, are hydrogen, halogen, alkyl (containing 1-5 carbon atoms), aryl, arylalkyl, or sulfo. The dyes are used to make novel conjugates with members of specific binding pairs that are ligands or receptors.